GB813539A - Improvements in the production of organic compounds with aliphatic conjugated unsaturated linkages - Google Patents
Improvements in the production of organic compounds with aliphatic conjugated unsaturated linkagesInfo
- Publication number
- GB813539A GB813539A GB26944/55A GB2694455A GB813539A GB 813539 A GB813539 A GB 813539A GB 26944/55 A GB26944/55 A GB 26944/55A GB 2694455 A GB2694455 A GB 2694455A GB 813539 A GB813539 A GB 813539A
- Authority
- GB
- United Kingdom
- Prior art keywords
- reacting
- beta
- product
- acid
- ylide
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 125000001931 aliphatic group Chemical group 0.000 title abstract 5
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- 150000002894 organic compounds Chemical class 0.000 title abstract 2
- 239000000047 product Substances 0.000 abstract 9
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 abstract 9
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 abstract 8
- -1 aromatic radical Chemical class 0.000 abstract 8
- KJPRLNWUNMBNBZ-UHFFFAOYSA-N cinnamic aldehyde Natural products O=CC=CC1=CC=CC=C1 KJPRLNWUNMBNBZ-UHFFFAOYSA-N 0.000 abstract 6
- KJPRLNWUNMBNBZ-QPJJXVBHSA-N (E)-cinnamaldehyde Chemical compound O=C\C=C\C1=CC=CC=C1 KJPRLNWUNMBNBZ-QPJJXVBHSA-N 0.000 abstract 5
- 150000001728 carbonyl compounds Chemical class 0.000 abstract 5
- 238000010438 heat treatment Methods 0.000 abstract 5
- 150000003254 radicals Chemical class 0.000 abstract 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 4
- BHOMJBFLUFSZLW-UHFFFAOYSA-N benzylidene(triphenyl)-$l^{5}-phosphane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(C=1C=CC=CC=1)=CC1=CC=CC=C1 BHOMJBFLUFSZLW-UHFFFAOYSA-N 0.000 abstract 4
- 238000006243 chemical reaction Methods 0.000 abstract 4
- 229940117916 cinnamic aldehyde Drugs 0.000 abstract 4
- 229910000073 phosphorus hydride Inorganic materials 0.000 abstract 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 3
- 229910052783 alkali metal Inorganic materials 0.000 abstract 3
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 abstract 3
- 235000013734 beta-carotene Nutrition 0.000 abstract 3
- 239000011648 beta-carotene Substances 0.000 abstract 3
- MLUCVPSAIODCQM-NSCUHMNNSA-N crotonaldehyde Chemical compound C\C=C\C=O MLUCVPSAIODCQM-NSCUHMNNSA-N 0.000 abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract 3
- 239000001257 hydrogen Substances 0.000 abstract 3
- OJVAMHKKJGICOG-UHFFFAOYSA-N 2,5-hexanedione Chemical compound CC(=O)CCC(C)=O OJVAMHKKJGICOG-UHFFFAOYSA-N 0.000 abstract 2
- APISVOVOJVZIBA-UHFFFAOYSA-N 2-(triphenyl-$l^{5}-phosphanylidene)acetonitrile Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=CC#N)C1=CC=CC=C1 APISVOVOJVZIBA-UHFFFAOYSA-N 0.000 abstract 2
- VSMDCVLKAAVJFW-UHFFFAOYSA-N 3-methyl-5-(2,6,6-trimethylcyclohexen-1-yl)penta-2,4-dien-1-ol Chemical compound OCC=C(C)C=CC1=C(C)CCCC1(C)C VSMDCVLKAAVJFW-UHFFFAOYSA-N 0.000 abstract 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 abstract 2
- 150000001340 alkali metals Chemical class 0.000 abstract 2
- OENHQHLEOONYIE-UKMVMLAPSA-N all-trans beta-carotene Natural products CC=1CCCC(C)(C)C=1/C=C/C(/C)=C/C=C/C(/C)=C/C=C/C=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C OENHQHLEOONYIE-UKMVMLAPSA-N 0.000 abstract 2
- IDMGVRDNZFQORW-JWBAUCAFSA-N axerophthene Chemical compound C\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C IDMGVRDNZFQORW-JWBAUCAFSA-N 0.000 abstract 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 abstract 2
- MLUCVPSAIODCQM-UHFFFAOYSA-N crotonaldehyde Natural products CC=CC=O MLUCVPSAIODCQM-UHFFFAOYSA-N 0.000 abstract 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 abstract 2
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 abstract 2
- JFBRAUFNAQPWKO-UHFFFAOYSA-N ethyl 2-[methylidene(diphenyl)-$l^{5}-phosphanyl]benzoate Chemical compound CCOC(=O)C1=CC=CC=C1P(=C)(C=1C=CC=CC=1)C1=CC=CC=C1 JFBRAUFNAQPWKO-UHFFFAOYSA-N 0.000 abstract 2
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 abstract 2
- 229940093858 ethyl acetoacetate Drugs 0.000 abstract 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 2
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 abstract 2
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 abstract 2
- XLSMFKSTNGKWQX-UHFFFAOYSA-N hydroxyacetone Chemical compound CC(=O)CO XLSMFKSTNGKWQX-UHFFFAOYSA-N 0.000 abstract 2
- 150000002576 ketones Chemical class 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 abstract 2
- 229920006395 saturated elastomer Polymers 0.000 abstract 2
- 229910052708 sodium Inorganic materials 0.000 abstract 2
- 239000011734 sodium Substances 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 abstract 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-O triphenylphosphanium Chemical compound C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-O 0.000 abstract 2
- OENHQHLEOONYIE-JLTXGRSLSA-N β-Carotene Chemical compound CC=1CCCC(C)(C)C=1\C=C\C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C OENHQHLEOONYIE-JLTXGRSLSA-N 0.000 abstract 2
- PSQYTAPXSHCGMF-BQYQJAHWSA-N β-ionone Chemical compound CC(=O)\C=C\C1=C(C)CCCC1(C)C PSQYTAPXSHCGMF-BQYQJAHWSA-N 0.000 abstract 2
- SFEOKXHPFMOVRM-UHFFFAOYSA-N (+)-(S)-gamma-ionone Natural products CC(=O)C=CC1C(=C)CCCC1(C)C SFEOKXHPFMOVRM-UHFFFAOYSA-N 0.000 abstract 1
- MLBZLJCMHFCTQM-UHFFFAOYSA-N (2-methylphenyl)-diphenylphosphane Chemical class CC1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 MLBZLJCMHFCTQM-UHFFFAOYSA-N 0.000 abstract 1
- OPSSCPNCFKJCFR-ANKZSMJWSA-N (2e,4e)-3-methyl-5-(2,6,6-trimethylcyclohexen-1-yl)penta-2,4-dienal Chemical compound O=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C OPSSCPNCFKJCFR-ANKZSMJWSA-N 0.000 abstract 1
- WKRBKYFIJPGYQC-DUXPYHPUSA-N (E)-3-methylglutaconic acid Chemical compound OC(=O)CC(/C)=C/C(O)=O WKRBKYFIJPGYQC-DUXPYHPUSA-N 0.000 abstract 1
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 abstract 1
- XDHOEHJVXXTEDV-HWKANZROSA-N (e)-1-ethoxyprop-1-ene Chemical compound CCO\C=C\C XDHOEHJVXXTEDV-HWKANZROSA-N 0.000 abstract 1
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 abstract 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 abstract 1
- CVBUKMMMRLOKQR-UHFFFAOYSA-N 1-phenylbutane-1,3-dione Chemical compound CC(=O)CC(=O)C1=CC=CC=C1 CVBUKMMMRLOKQR-UHFFFAOYSA-N 0.000 abstract 1
- XOAUNGGNONXOND-UHFFFAOYSA-N 2,7-dimethylocta-1,3-diene Chemical compound CC(C)CCC=CC(C)=C XOAUNGGNONXOND-UHFFFAOYSA-N 0.000 abstract 1
- PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 abstract 1
- OVXJWSYBABKZMD-UHFFFAOYSA-N 2-chloro-1,1-diethoxyethane Chemical compound CCOC(CCl)OCC OVXJWSYBABKZMD-UHFFFAOYSA-N 0.000 abstract 1
- BTOVVHWKPVSLBI-UHFFFAOYSA-N 2-methylprop-1-enylbenzene Chemical group CC(C)=CC1=CC=CC=C1 BTOVVHWKPVSLBI-UHFFFAOYSA-N 0.000 abstract 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 abstract 1
- YOYODHNOTKUUDY-UHFFFAOYSA-N 3-methyl-5-(2,6,6-trimethylcyclohexen-1-yl)penta-2,4-dienenitrile Chemical compound N#CC=C(C)C=CC1=C(C)CCCC1(C)C YOYODHNOTKUUDY-UHFFFAOYSA-N 0.000 abstract 1
- JDCCCHBBXRQRGU-UHFFFAOYSA-N 5-phenylpenta-2,4-dienenitrile Chemical compound N#CC=CC=CC1=CC=CC=C1 JDCCCHBBXRQRGU-UHFFFAOYSA-N 0.000 abstract 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 abstract 1
- SHGAZHPCJJPHSC-ZVCIMWCZSA-N 9-cis-retinoic acid Chemical compound OC(=O)/C=C(\C)/C=C/C=C(/C)\C=C\C1=C(C)CCCC1(C)C SHGAZHPCJJPHSC-ZVCIMWCZSA-N 0.000 abstract 1
- UMHJEEQLYBKSAN-UHFFFAOYSA-N Adipaldehyde Chemical compound O=CCCCCC=O UMHJEEQLYBKSAN-UHFFFAOYSA-N 0.000 abstract 1
- CAHQGWAXKLQREW-UHFFFAOYSA-N Benzal chloride Chemical class ClC(Cl)C1=CC=CC=C1 CAHQGWAXKLQREW-UHFFFAOYSA-N 0.000 abstract 1
- ZNSMNVMLTJELDZ-UHFFFAOYSA-N Bis(2-chloroethyl)ether Chemical compound ClCCOCCCl ZNSMNVMLTJELDZ-UHFFFAOYSA-N 0.000 abstract 1
- NBCVCMJHCIFNGF-UHFFFAOYSA-N CCC(C)CC=C.C(C=C1)=CC=C1P(C1=CC=CC=C1)C1=CC=CC=C1 Chemical compound CCC(C)CC=C.C(C=C1)=CC=C1P(C1=CC=CC=C1)C1=CC=CC=C1 NBCVCMJHCIFNGF-UHFFFAOYSA-N 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 1
- RENMDAKOXSCIGH-UHFFFAOYSA-N Chloroacetonitrile Chemical compound ClCC#N RENMDAKOXSCIGH-UHFFFAOYSA-N 0.000 abstract 1
- 241000723346 Cinnamomum camphora Species 0.000 abstract 1
- ZNZYKNKBJPZETN-WELNAUFTSA-N Dialdehyde 11678 Chemical compound N1C2=CC=CC=C2C2=C1[C@H](C[C@H](/C(=C/O)C(=O)OC)[C@@H](C=C)C=O)NCC2 ZNZYKNKBJPZETN-WELNAUFTSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 241000575946 Ione Species 0.000 abstract 1
- PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 abstract 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 abstract 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract 1
- MKYQPGPNVYRMHI-UHFFFAOYSA-N Triphenylethylene Chemical group C=1C=CC=CC=1C=C(C=1C=CC=CC=1)C1=CC=CC=C1 MKYQPGPNVYRMHI-UHFFFAOYSA-N 0.000 abstract 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000001299 aldehydes Chemical class 0.000 abstract 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 abstract 1
- 150000001342 alkaline earth metals Chemical class 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- ANVAOWXLWRTKGA-XHGAXZNDSA-N all-trans-alpha-carotene Natural products CC=1CCCC(C)(C)C=1/C=C/C(/C)=C/C=C/C(/C)=C/C=C/C=C(C)C=CC=C(C)C=CC1C(C)=CCCC1(C)C ANVAOWXLWRTKGA-XHGAXZNDSA-N 0.000 abstract 1
- 125000003368 amide group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000004429 atom Chemical group 0.000 abstract 1
- 125000002648 azanetriyl group Chemical group *N(*)* 0.000 abstract 1
- IZALUMVGBVKPJD-UHFFFAOYSA-N benzene-1,3-dicarbaldehyde Chemical class O=CC1=CC=CC(C=O)=C1 IZALUMVGBVKPJD-UHFFFAOYSA-N 0.000 abstract 1
- 239000012965 benzophenone Substances 0.000 abstract 1
- TUPZEYHYWIEDIH-WAIFQNFQSA-N beta-carotene Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CCCC1(C)C)C=CC=C(/C)C=CC2=CCCCC2(C)C TUPZEYHYWIEDIH-WAIFQNFQSA-N 0.000 abstract 1
- 150000001579 beta-carotenes Chemical class 0.000 abstract 1
- WKRBKYFIJPGYQC-UHFFFAOYSA-N beta-methylglutaconic acid Natural products OC(=O)CC(C)=CC(O)=O WKRBKYFIJPGYQC-UHFFFAOYSA-N 0.000 abstract 1
- 229960002747 betacarotene Drugs 0.000 abstract 1
- 238000009835 boiling Methods 0.000 abstract 1
- 239000001273 butane Substances 0.000 abstract 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 229960000846 camphor Drugs 0.000 abstract 1
- 229930008380 camphor Natural products 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- 239000003153 chemical reaction reagent Substances 0.000 abstract 1
- VXIVSQZSERGHQP-UHFFFAOYSA-N chloroacetamide Chemical compound NC(=O)CCl VXIVSQZSERGHQP-UHFFFAOYSA-N 0.000 abstract 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical class OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 abstract 1
- 238000004587 chromatography analysis Methods 0.000 abstract 1
- 125000000490 cinnamyl group Chemical group C(C=CC1=CC=CC=C1)* 0.000 abstract 1
- 238000001816 cooling Methods 0.000 abstract 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 abstract 1
- NZZIMKJIVMHWJC-UHFFFAOYSA-N dibenzoylmethane Chemical compound C=1C=CC=CC=1C(=O)CC(=O)C1=CC=CC=C1 NZZIMKJIVMHWJC-UHFFFAOYSA-N 0.000 abstract 1
- VWWMOACCGFHMEV-UHFFFAOYSA-N dicarbide(2-) Chemical compound [C-]#[C-] VWWMOACCGFHMEV-UHFFFAOYSA-N 0.000 abstract 1
- 125000005594 diketone group Chemical group 0.000 abstract 1
- 150000002009 diols Chemical class 0.000 abstract 1
- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 abstract 1
- 238000004821 distillation Methods 0.000 abstract 1
- 125000004185 ester group Chemical group 0.000 abstract 1
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 abstract 1
- 125000001033 ether group Chemical group 0.000 abstract 1
- 150000002170 ethers Chemical class 0.000 abstract 1
- DBWOGUVMJLALME-UHFFFAOYSA-N ethyl 3-hydroxy-2-methylbut-2-enoate Chemical compound CCOC(=O)C(C)=C(C)O DBWOGUVMJLALME-UHFFFAOYSA-N 0.000 abstract 1
- UTXVCHVLDOLVPC-UHFFFAOYSA-N ethyl 3-methylbut-2-enoate Chemical compound CCOC(=O)C=C(C)C UTXVCHVLDOLVPC-UHFFFAOYSA-N 0.000 abstract 1
- NLKBBWBCWHTRAJ-UHFFFAOYSA-N ethyl 5-phenylpenta-2,4-dienoate Chemical compound CCOC(=O)C=CC=CC1=CC=CC=C1 NLKBBWBCWHTRAJ-UHFFFAOYSA-N 0.000 abstract 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 abstract 1
- JGEMYUOFGVHXKV-OWOJBTEDSA-N fumaraldehyde Chemical compound O=C\C=C\C=O JGEMYUOFGVHXKV-OWOJBTEDSA-N 0.000 abstract 1
- HNZUNIKWNYHEJJ-UHFFFAOYSA-N geranyl acetone Natural products CC(C)=CCCC(C)=CCCC(C)=O HNZUNIKWNYHEJJ-UHFFFAOYSA-N 0.000 abstract 1
- 125000002350 geranyl group Chemical group [H]C([*])([H])/C([H])=C(C([H])([H])[H])/C([H])([H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 abstract 1
- 229940015043 glyoxal Drugs 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 150000002430 hydrocarbons Chemical class 0.000 abstract 1
- 150000002431 hydrogen Chemical group 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 239000012433 hydrogen halide Substances 0.000 abstract 1
- 229910000039 hydrogen halide Inorganic materials 0.000 abstract 1
- 238000005984 hydrogenation reaction Methods 0.000 abstract 1
- 239000013067 intermediate product Substances 0.000 abstract 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 abstract 1
- 229910052740 iodine Inorganic materials 0.000 abstract 1
- 239000011630 iodine Substances 0.000 abstract 1
- 229910052744 lithium Inorganic materials 0.000 abstract 1
- LGRLWUINFJPLSH-UHFFFAOYSA-N methanide Chemical compound [CH3-] LGRLWUINFJPLSH-UHFFFAOYSA-N 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 abstract 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 abstract 1
- 230000003472 neutralizing effect Effects 0.000 abstract 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 abstract 1
- 150000004714 phosphonium salts Chemical group 0.000 abstract 1
- 229910052698 phosphorus Inorganic materials 0.000 abstract 1
- 239000011574 phosphorus Substances 0.000 abstract 1
- IJNJLGFTSIAHEA-UHFFFAOYSA-N prop-2-ynal Chemical compound O=CC#C IJNJLGFTSIAHEA-UHFFFAOYSA-N 0.000 abstract 1
- YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical class BrCC#C YORCIIVHUBAYBQ-UHFFFAOYSA-N 0.000 abstract 1
- JXJIQCXXJGRKRJ-KOOBJXAQSA-N pseudoionone Chemical compound CC(C)=CCC\C(C)=C\C=C\C(C)=O JXJIQCXXJGRKRJ-KOOBJXAQSA-N 0.000 abstract 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- 238000001953 recrystallisation Methods 0.000 abstract 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 abstract 1
- 235000010199 sorbic acid Nutrition 0.000 abstract 1
- 239000004334 sorbic acid Substances 0.000 abstract 1
- 229940075582 sorbic acid Drugs 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- MDDUHVRJJAFRAU-YZNNVMRBSA-N tert-butyl-[(1r,3s,5z)-3-[tert-butyl(dimethyl)silyl]oxy-5-(2-diphenylphosphorylethylidene)-4-methylidenecyclohexyl]oxy-dimethylsilane Chemical compound C1[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)C(=C)\C1=C/CP(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 MDDUHVRJJAFRAU-YZNNVMRBSA-N 0.000 abstract 1
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 abstract 1
- MEBONNVPKOBPEA-UHFFFAOYSA-N trimethyl cyclohexane Natural products CC1CCCCC1(C)C MEBONNVPKOBPEA-UHFFFAOYSA-N 0.000 abstract 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 abstract 1
- 229920002554 vinyl polymer Polymers 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
- C07C403/24—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by six-membered non-aromatic rings, e.g. beta-carotene
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
- C07C403/02—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains containing only carbon and hydrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
- C07C403/20—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by carboxyl groups or halides, anhydrides, or (thio)esters thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/511—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups
- C07C45/515—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups the singly bound functional group being an acetalised, ketalised hemi-acetalised, or hemi-ketalised hydroxyl group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/535—Organo-phosphoranes
- C07F9/5352—Phosphoranes containing the structure P=C-
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
A process for the production of organic compounds with aliphatic conjugated unsaturated linkages comprises adding to a phosphine ylide of the general formula: <FORM:0813539/IV (b)/1> in which each R represents an aryl group, R1 represents hydrogen or an aliphatic group and R11 represents hydrogen, a saturated or unsaturated aliphatic, cycloaliphatic, cycloaliphatic-aliphatic, araliphatic or aromatic radical or the radical <FORM:0813539/IV (b)/2> R111 representing the link between the two carbon atoms adjacent to the phosphorus which link consists of at least one atom, R1111 being hydrogen or alkyl, or R1 and R11 jointly with the C to which they are attached represent a cycloaliphatic radical, wherein each of the radicals R1, R11 and R111 can bear indifferent groups, such as ester groups, nitrilo groups, and amide groups, ether groups and aromatically bound halogen, about the equivalent amount of a saturated or unsaturated carbonyl compound whereby a product of the general formula: <FORM:0813539/IV (b)/3> is formed, X being the radical originating from the carbonyl compound and R1 and R11 having the meaning given above except that when bisylides are reacted R11 is <FORM:0813539/IV (b)/4> R111 and R1111 having the meaning given above, with the proviso that the system of aliphatic conjugated unsaturated linkages exists at least in one of the radicals R1 or R11 or in the carbonyl compound or is formed by the reaction of the phosphine ylide with the carbonyl compound. The phosphine ylides employed as starting materials may be prepared by reacting triphenyl, tritolyl or diphenyltolyl phosphines with organic halides such as methyl, ethyl, allyl, cyclohexyl, diphenylmethyl, cinnamyl, geranyl, cyclogeranyl, a - and b -ionyl or propargyl bromides, methoxybenzyl or chlorbenzyl chlorides, chloracetic acid esters, chloracetaldehyde diethyl acetal or chloro-acetonitrile, monochlorethyl ether and chloracetamide, dibrompropane or butane or 1 : 4-dichlorobutene-(2) preferably by heating equivalent amounts of reactants e.g. in ethers or hydrocarbons as solvents, to obtain quaternary phosphonium salts and treating the latter with hydrogen halide removing reagents which do not form water in the reaction, e.g. methyl, phenyl, butyl or tolyl lithium phenyl, ethyl or tertiary butyl magnesium halides, an alkali metal, e.g. sodium, acetylide, an alkali metal amide, or alkali metal or alkaline earth metal alcoholates. Solvents mentioned for use in the ylide forming reaction are ether, tetrahydrofurane and dioxane, preferably in an oxygen-free atmosphere. Carbonyl compounds mentioned in addition to those employed in the examples include acetaldehyde, cyclohexanone, acetophenone, p,p1-tetramethyldiaminobenzophenone, p,p1-dinitrobenzophenone, propargyl aldehyde, butine-(1)-one-(3), pseudoionone, camphor, ethyl acetoacetate, acetol, furfural, pyridine aldehydes and ketones, dialdehydes and diketones, e.g. glyoxal, maleic and succinic dialdehydes, adipaldehyde, terephthal- and isophthal-aldehydes, bromomalonic dialdehyde, acetyl-acetone, acetonyl acetone, benzoyl-acetone, di-benzoyl methane, 4.9 - dimethyldodecapentaene - (2.6.7.8.10) diol (1.12), 2,7 - dimethyloctadien - (3.5) dione-(2.7) and 2.7-dimethyl octaene-(4)-dione (2.7). The reaction of the phosphine ylide and aldehyde or ketone may be carried out with cooling, the intermediate product decomposed by heating and the reaction product worked up, after removal of phosphine oxide, by chromatography and or distillation or recrystallisation. In examples: 1-phenylbutadiene-(1.3) is obtained by reacting triphenylphosphonium vinyl methylide with benzaldehyde (1); 1.4-diphenylbutadiene is obtained by reacting triphenylphosphonium benzylide with cinnamaldehyde (2-4); 1 - 10 - diphenyl - 3.8 - dimethyl - decapentaene - (1.3.5.7.9) is obtained by reacting 2.7 - dimethyloctadiene - (2.6) - dial - (1.8) with triphenylphosphonium benzylide (5); 1.10-bis-(21.61.61 - trimethylcyclohexene (11) - yl - (11)-3.8 - dimethyl - decatetraene (1.3.7.9) ine (5) is obtained by reacting 2.7-dimethyloctadiene (2.6)-ine (4)-dial (1.8) with triphenyl phosphonium beta - cyclogeranylide (6); 11,12-dehydroaxerophthene is obtianed by reacting beta - ione with triphenylphosphonium 4-methyl - hexene - (2) - ene - (4) - ylide (1) and may be converted by hydrogenation to axerophthene (7); 1.10-diphenyldecapentaene is obtained by reacting cinnamaldehyde with the bis-ylide obtained by treating 2-butene-1.4-bis-(triphenylphosphonium) chloride with phenyl lithium (8); 1.4-diphenylbutadiene is obtained by reacting triphenyl phosphonium benzylide with cinnamaldehyd (9-11); 1-phenyl-2-methyl propylene and 1,2,2-triphenylethylene are similarly obtained using acetone and benzophenone (11); cinnamalacetic acid ethyl ester, beta - methyl - beta - hydroxy - methylacrylic acid ethyl ester, sorbic ester, beta, beta-dimethyl acrylic acid ethyl ester and beta-methylglutaconic acid diethyl ester are obtained by reacting cinnamaldehyde, acetol, crotonaldehyde, acetone, ethylacetoacetate with carbethoxy methylene triphenylphosphine (12); cinnamalacetonitrile and beta-ionyl-idene acetonitrile respectively are obtained by reacting cinnamaldehyde and betaionone with cyanomethylene triphenylphosphine (13); sorbic acid amide is obtained by reacting carbamidoethylene triphenylphosphine or its alcohol addition product with crotonaldehyde (14); 1,10-bis - (21.61.61 - trimethylcyclohexane - (11) - yl-) 3.8 - dimethyldecapentaene (1.3.5.7.9) is obtained by reacting 2.7-dimethyloctatrien (2.4.6)-dial-1.8 with betacyclogeranyl triphenylphosphine (15); isomeric beta carotenes, which may be converted into all-trans-beta carotene by boiling the solution with a trace of iodine, are obtained by reacting triphenylphosphonium-beta ionylide with 4.9-dimethyldodecapentaene-(2.4.6.8.10)-dial-(1.12), (16); trans Vitamin A acid methyl ester, which is saponified to obtain the corresponding free acid, is obtained by reacting beta-ionylideneacetaldehyde with the product obtained by reacting gamma-bromomethyl crotonic acid methyl ester with triphenyl phosphine and treating the product with sodium ethoxide solution (17); and 15, 151-dehydrobeta-carotene is obtained by reacting 2.7-dimethyloctadiene - (2.6) - ine - (4) - dial - (1.8) with the phosphonium ylide obtained by reacting beta-ionylidene ethanol with phosphorus tribromide, reacting the product with triphenyl phosphine and treating the phosphonium halide with a solution of sodium in ethanol; the product being optionally converted to betacarotene by treatment with iodine (18). 2.7 - Dimethyloctatrien - (2.4.6) - diol - (1.8) is obtained by reacting maleic dialdehyde tetraethyl lacetal with propenyl ethyl ether, neutralizing and distilling the product to obtain 2.7-dimethyl-1.1.3.6.8-8-hexaethoxyoctaene and heating the latter with p-toluene sulphonic acid. 4.9 - Dimethyldodecapentaene - (2.4.6.8.10) dial - (1.12) is obtained by heating the above product with ethyl orthoformate and ammonium nitrate to obtain 1.1.8.8-tetraethoxy 2.7-dimethyloctatriene which is reacted with vinyl ethyl ether and heating the product with p-toluene sulphonic acid.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE813539X | 1954-09-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB813539A true GB813539A (en) | 1959-05-21 |
Family
ID=6733609
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB26944/55A Expired GB813539A (en) | 1954-09-24 | 1955-09-21 | Improvements in the production of organic compounds with aliphatic conjugated unsaturated linkages |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB813539A (en) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1160855B (en) * | 1961-11-08 | 1964-01-09 | Bayer Ag | Process for the preparation of propargyl phosphonium halides |
| US3274228A (en) * | 1963-07-29 | 1966-09-20 | Interchem Corp | Triphenylphosphinemethylene compounds |
| US3459772A (en) * | 1965-07-01 | 1969-08-05 | Hoffmann La Roche | Ethylenedioxy substituted benz(e)indenes |
| US3935275A (en) * | 1968-07-03 | 1976-01-27 | Givaudan Corporation | Process for preparation of terpene flavorants and novel intermediates therefor |
| EP0018532A1 (en) * | 1979-04-23 | 1980-11-12 | Bayer Ag | 1-Aryl-4-methyl-penta-1,2-dienes, process for their preparation and their use for the preparation of 3-(2-aryl-vinyl)-2,2-dimethylcyclopropane-1-carboxylates |
| EP0019089A1 (en) * | 1979-04-23 | 1980-11-26 | Bayer Ag | 5-Aryl-3-(1'-halogen-1'-methyl)ethyl-pent-4-en-carboxylic acid esters, process for their preparation, and their use for the preparation of 3-(2-arylvinyl)-2,2-dimethyl-cyclopropane-1-carboxylic acid esters |
| EP0019713A1 (en) * | 1979-04-23 | 1980-12-10 | Bayer Ag | Process for the preparation of styryl-cyclopropane carboxylates, intermediates therefor and their production |
| CN114057790A (en) * | 2021-11-18 | 2022-02-18 | 万华化学集团股份有限公司 | Preparation method of vitamin A triphenylphosphine salt with high all-trans isomer content |
-
1955
- 1955-09-21 GB GB26944/55A patent/GB813539A/en not_active Expired
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1160855B (en) * | 1961-11-08 | 1964-01-09 | Bayer Ag | Process for the preparation of propargyl phosphonium halides |
| US3274228A (en) * | 1963-07-29 | 1966-09-20 | Interchem Corp | Triphenylphosphinemethylene compounds |
| US3459772A (en) * | 1965-07-01 | 1969-08-05 | Hoffmann La Roche | Ethylenedioxy substituted benz(e)indenes |
| US3935275A (en) * | 1968-07-03 | 1976-01-27 | Givaudan Corporation | Process for preparation of terpene flavorants and novel intermediates therefor |
| EP0018532A1 (en) * | 1979-04-23 | 1980-11-12 | Bayer Ag | 1-Aryl-4-methyl-penta-1,2-dienes, process for their preparation and their use for the preparation of 3-(2-aryl-vinyl)-2,2-dimethylcyclopropane-1-carboxylates |
| EP0019089A1 (en) * | 1979-04-23 | 1980-11-26 | Bayer Ag | 5-Aryl-3-(1'-halogen-1'-methyl)ethyl-pent-4-en-carboxylic acid esters, process for their preparation, and their use for the preparation of 3-(2-arylvinyl)-2,2-dimethyl-cyclopropane-1-carboxylic acid esters |
| EP0019713A1 (en) * | 1979-04-23 | 1980-12-10 | Bayer Ag | Process for the preparation of styryl-cyclopropane carboxylates, intermediates therefor and their production |
| CN114057790A (en) * | 2021-11-18 | 2022-02-18 | 万华化学集团股份有限公司 | Preparation method of vitamin A triphenylphosphine salt with high all-trans isomer content |
| CN114057790B (en) * | 2021-11-18 | 2023-10-24 | 万华化学集团股份有限公司 | Preparation method of vitamin A triphenylphosphine salt with high all-trans isomer content |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Heck | The arylation of allylic alcohols with organopalladium compounds. A new synthesis of 3-aryl aldehydes and ketones | |
| Kozikowski et al. | Phosphoniosilylation. An efficient and practical method for the. beta.-functionalization of enones | |
| US2847478A (en) | Allyl transetherification | |
| GB813539A (en) | Improvements in the production of organic compounds with aliphatic conjugated unsaturated linkages | |
| US3932462A (en) | Manufacture of unsaturated ketones | |
| US3145232A (en) | Ozonization and reduction of unsaturated organic compounds | |
| Sandler | Cyanuric chloride. Novel laboratory hydrochlorinating reagent for alcohols | |
| Welch et al. | A stereoselective total synthesis of (.+-.)-gymnomitrol | |
| Klein et al. | Reaction of Grignard reagents with. alpha.-bromocrotonic and. alpha.-bromocinnamic acids | |
| Ipatieff et al. | CONDENSATION OF KETONES WITH ALCOHOLS IN THE PRESENCE OF MIXED CATALYSTS1 | |
| US3057888A (en) | Processes for and intermediates in the manufacture of unsaturated aldehydes and ketones | |
| US2246032A (en) | Process for the production of beta gamma unsaturated ketones | |
| US2543312A (en) | Resinous acetals and process for producing and hydrolyzing the same to produce unsaturated aldehydes | |
| US2481157A (en) | Treatment of halo-hydrocarbons | |
| US2811561A (en) | Hjc chi | |
| US4263443A (en) | Conversion of aldehydes | |
| US3439042A (en) | Synthesis of pseudoionones | |
| Parham et al. | Steric effects in the solvolysis of cis-and trans-13, 13-dichlorobicyclo] 10.1. 0] tridecane | |
| US3927076A (en) | Method of rearranging tertiary vinyl carbinols | |
| Ishihara et al. | Novel synthesis of dienones and enones from propargyl alcohols and allyl alcohols with 2, 2-dimethoxypropane: Synthesis of ionone and irone | |
| US3463823A (en) | Divinyl acetals by dehydrohalogenation of bis(2-haloethyl) acetals | |
| US2987551A (en) | Preparation of citral | |
| US2299189A (en) | Vinyl ether | |
| US2172803A (en) | Polycarboxylic acid esters | |
| US2421559A (en) | Acetals of pyruvic aldehyde |