IE910907A1 - Process for the preparation of acylals - Google Patents
Process for the preparation of acylalsInfo
- Publication number
- IE910907A1 IE910907A1 IE090791A IE90791A IE910907A1 IE 910907 A1 IE910907 A1 IE 910907A1 IE 090791 A IE090791 A IE 090791A IE 90791 A IE90791 A IE 90791A IE 910907 A1 IE910907 A1 IE 910907A1
- Authority
- IE
- Ireland
- Prior art keywords
- alkyl
- formula
- groups
- acetoxymethoxy
- compound
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 23
- 238000002360 preparation method Methods 0.000 title claims description 11
- 150000008063 acylals Chemical class 0.000 title description 8
- 150000001875 compounds Chemical class 0.000 claims abstract description 22
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims abstract description 14
- 150000008064 anhydrides Chemical class 0.000 claims abstract description 9
- -1 benzyloxy, benzylthio, benzylamino, dibenzylamino Chemical group 0.000 claims description 33
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 125000002252 acyl group Chemical group 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
- 150000002431 hydrogen Chemical class 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 125000003282 alkyl amino group Chemical group 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 150000007524 organic acids Chemical class 0.000 claims description 5
- 239000011541 reaction mixture Substances 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 238000003756 stirring Methods 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000004442 acylamino group Chemical group 0.000 claims description 2
- 125000004423 acyloxy group Chemical group 0.000 claims description 2
- 125000005035 acylthio group Chemical group 0.000 claims description 2
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 125000002837 carbocyclic group Chemical group 0.000 claims description 2
- 150000001735 carboxylic acids Chemical class 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- 125000005544 phthalimido group Chemical group 0.000 claims description 2
- 239000000376 reactant Substances 0.000 claims 2
- 239000002253 acid Substances 0.000 abstract description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- 239000001294 propane Substances 0.000 description 8
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 239000013067 intermediate product Substances 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 229960004132 diethyl ether Drugs 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 238000004508 fractional distillation Methods 0.000 description 2
- 229940093915 gynecological organic acid Drugs 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- LLBQTJOIARBALH-UHFFFAOYSA-N (1-phenoxy-3-propan-2-yloxypropan-2-yl)oxymethyl acetate Chemical compound CC(=O)OCOC(COC(C)C)COC1=CC=CC=C1 LLBQTJOIARBALH-UHFFFAOYSA-N 0.000 description 1
- XWFZAAHRVJIMOT-UHFFFAOYSA-N (3-ethylsulfanyl-2-phenylmethoxypropoxy)methyl acetate Chemical compound CC(=O)OCOCC(CSCC)OCC1=CC=CC=C1 XWFZAAHRVJIMOT-UHFFFAOYSA-N 0.000 description 1
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 description 1
- AJJGRBMYVRSEES-UHFFFAOYSA-N 1,3-di(propan-2-yloxy)propan-2-ol Chemical compound CC(C)OCC(O)COC(C)C AJJGRBMYVRSEES-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- NWLUZGJDEZBBRH-UHFFFAOYSA-N 2-(propan-2-yloxymethyl)oxirane Chemical compound CC(C)OCC1CO1 NWLUZGJDEZBBRH-UHFFFAOYSA-N 0.000 description 1
- XWPSEWNIMZEDRN-UHFFFAOYSA-N 2-methoxyethoxymethyl acetate Chemical compound COCCOCOC(C)=O XWPSEWNIMZEDRN-UHFFFAOYSA-N 0.000 description 1
- SXLXOPPFWKCKMN-UHFFFAOYSA-N 2-phenoxyethoxymethyl acetate Chemical compound CC(=O)OCOCCOC1=CC=CC=C1 SXLXOPPFWKCKMN-UHFFFAOYSA-N 0.000 description 1
- QEPNPSXRQRFIOO-UHFFFAOYSA-N 2-phenylmethoxyethoxymethyl acetate Chemical compound CC(=O)OCOCCOCC1=CC=CC=C1 QEPNPSXRQRFIOO-UHFFFAOYSA-N 0.000 description 1
- 101150041968 CDC13 gene Proteins 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 241001521416 Leva Species 0.000 description 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
- DYJGTMNKFZBZRP-UHFFFAOYSA-N [2-(acetyloxymethoxy)-3-phenylmethoxypropyl] 2,2-dimethylpropanoate Chemical compound CC(=O)OCOC(COC(=O)C(C)(C)C)COCC1=CC=CC=C1 DYJGTMNKFZBZRP-UHFFFAOYSA-N 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 125000002015 acyclic group Chemical group 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 238000010936 aqueous wash Methods 0.000 description 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 229940052303 ethers for general anesthesia Drugs 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 150000002373 hemiacetals Chemical class 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 238000007327 hydrogenolysis reaction Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- LSACYLWPPQLVSM-UHFFFAOYSA-N isobutyric acid anhydride Chemical compound CC(C)C(=O)OC(=O)C(C)C LSACYLWPPQLVSM-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000009183 running Effects 0.000 description 1
- LMHHRCOWPQNFTF-UHFFFAOYSA-N s-propan-2-yl azepane-1-carbothioate Chemical compound CC(C)SC(=O)N1CCCCCC1 LMHHRCOWPQNFTF-UHFFFAOYSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
- MJURLCYUAJXTOU-UHFFFAOYSA-N sulfinyl(sulfinylmethoxy)methane Chemical class O=S=COC=S=O MJURLCYUAJXTOU-UHFFFAOYSA-N 0.000 description 1
- 150000004072 triols Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Indole Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Saccharide Compounds (AREA)
- Steroid Compounds (AREA)
- Cephalosporin Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4008856A DE4008856A1 (de) | 1990-03-20 | 1990-03-20 | Verfahren zur herstellung von acylalen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| IE910907A1 true IE910907A1 (en) | 1991-09-25 |
Family
ID=6402600
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE090791A IE910907A1 (en) | 1990-03-20 | 1991-03-19 | Process for the preparation of acylals |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US5231221A (enExample) |
| EP (1) | EP0448006B1 (enExample) |
| JP (1) | JP3010076B2 (enExample) |
| AT (1) | ATE117670T1 (enExample) |
| DE (2) | DE4008856A1 (enExample) |
| DK (1) | DK0448006T3 (enExample) |
| ES (1) | ES2068410T3 (enExample) |
| GR (1) | GR3015102T3 (enExample) |
| IE (1) | IE910907A1 (enExample) |
| PT (1) | PT97072A (enExample) |
| TW (1) | TW206211B (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4444669A1 (de) * | 1994-12-15 | 1996-06-20 | Hoechst Ag | Strahlungsempfindliches Gemisch |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB830850A (en) * | 1957-11-07 | 1960-03-23 | Distillers Co Yeast Ltd | Production of alkoxymethyl acetates |
| US3165532A (en) * | 1961-06-14 | 1965-01-12 | Exxon Research Engineering Co | Hemiacetal ester production |
-
1990
- 1990-03-20 DE DE4008856A patent/DE4008856A1/de not_active Withdrawn
-
1991
- 1991-03-18 ES ES91104127T patent/ES2068410T3/es not_active Expired - Lifetime
- 1991-03-18 EP EP91104127A patent/EP0448006B1/de not_active Expired - Lifetime
- 1991-03-18 US US07/671,103 patent/US5231221A/en not_active Expired - Fee Related
- 1991-03-18 DK DK91104127.5T patent/DK0448006T3/da active
- 1991-03-18 DE DE59104352T patent/DE59104352D1/de not_active Expired - Fee Related
- 1991-03-18 AT AT91104127T patent/ATE117670T1/de not_active IP Right Cessation
- 1991-03-19 JP JP3078291A patent/JP3010076B2/ja not_active Expired - Lifetime
- 1991-03-19 PT PT97072A patent/PT97072A/pt not_active Application Discontinuation
- 1991-03-19 IE IE090791A patent/IE910907A1/en unknown
- 1991-03-26 TW TW080102324A patent/TW206211B/zh active
-
1995
- 1995-02-17 GR GR950400320T patent/GR3015102T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GR3015102T3 (en) | 1995-05-31 |
| DE4008856A1 (de) | 1991-09-26 |
| DE59104352D1 (de) | 1995-03-09 |
| PT97072A (pt) | 1991-12-31 |
| DK0448006T3 (da) | 1995-06-19 |
| EP0448006A2 (de) | 1991-09-25 |
| JP3010076B2 (ja) | 2000-02-14 |
| JPH04217941A (ja) | 1992-08-07 |
| ES2068410T3 (es) | 1995-04-16 |
| ATE117670T1 (de) | 1995-02-15 |
| TW206211B (enExample) | 1993-05-21 |
| EP0448006A3 (en) | 1992-04-22 |
| EP0448006B1 (de) | 1995-01-25 |
| US5231221A (en) | 1993-07-27 |
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