JPS595133A - β−アルコキシケトン類およびβ−ケトアセタ−ル類の製法 - Google Patents
β−アルコキシケトン類およびβ−ケトアセタ−ル類の製法Info
- Publication number
- JPS595133A JPS595133A JP57111600A JP11160082A JPS595133A JP S595133 A JPS595133 A JP S595133A JP 57111600 A JP57111600 A JP 57111600A JP 11160082 A JP11160082 A JP 11160082A JP S595133 A JPS595133 A JP S595133A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- formula
- group
- phenyl
- methyl
- 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.)
- Granted
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 55
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 25
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 17
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 12
- 238000004519 manufacturing process Methods 0.000 claims description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- -1 enamine compound Chemical class 0.000 abstract description 23
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 abstract description 19
- 239000002841 Lewis acid Substances 0.000 abstract description 9
- 150000007517 lewis acids Chemical class 0.000 abstract description 9
- 239000002904 solvent Substances 0.000 abstract description 4
- 150000008282 halocarbons Chemical class 0.000 abstract description 3
- 239000003814 drug Substances 0.000 abstract description 2
- 239000000126 substance Substances 0.000 abstract description 2
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 abstract 1
- 239000003905 agrochemical Substances 0.000 abstract 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 13
- 150000001241 acetals Chemical class 0.000 description 12
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 12
- 238000000034 method Methods 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 9
- JARKCYVAAOWBJS-UHFFFAOYSA-N hexanal Chemical compound CCCCCC=O JARKCYVAAOWBJS-UHFFFAOYSA-N 0.000 description 8
- PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 description 6
- 238000009835 boiling Methods 0.000 description 5
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 4
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- SPEUIVXLLWOEMJ-UHFFFAOYSA-N acetaldehyde dimethyl acetal Natural products COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 3
- 238000005292 vacuum distillation Methods 0.000 description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 2
- 229910015900 BF3 Inorganic materials 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 150000001728 carbonyl compounds Chemical class 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- DTUQWGWMVIHBKE-UHFFFAOYSA-N phenylacetaldehyde Chemical compound O=CCC1=CC=CC=C1 DTUQWGWMVIHBKE-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- ASYRYAHIFYGVSH-UHFFFAOYSA-N 2-(1-ethoxyethyl)cyclohexan-1-one Chemical compound CCOC(C)C1CCCCC1=O ASYRYAHIFYGVSH-UHFFFAOYSA-N 0.000 description 1
- UVTSUSLMEDDPHJ-UHFFFAOYSA-N 2-(dimethoxymethyl)cyclohexan-1-one Chemical compound COC(OC)C1CCCCC1=O UVTSUSLMEDDPHJ-UHFFFAOYSA-N 0.000 description 1
- JHNCIGGWJHJOSK-UHFFFAOYSA-N 2-(ethoxymethyl)cyclohexan-1-one Chemical compound CCOCC1CCCCC1=O JHNCIGGWJHJOSK-UHFFFAOYSA-N 0.000 description 1
- OXQGTIUCKGYOAA-UHFFFAOYSA-N 2-Ethylbutanoic acid Chemical compound CCC(CC)C(O)=O OXQGTIUCKGYOAA-UHFFFAOYSA-N 0.000 description 1
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 1
- VNYKMATXHYMXFE-UHFFFAOYSA-N 2-methoxy-4-methyloxane Chemical compound COC1CC(C)CCO1 VNYKMATXHYMXFE-UHFFFAOYSA-N 0.000 description 1
- XTDKZSUYCXHXJM-UHFFFAOYSA-N 2-methoxyoxane Chemical compound COC1CCCCO1 XTDKZSUYCXHXJM-UHFFFAOYSA-N 0.000 description 1
- QANNWEQEHKZBDM-UHFFFAOYSA-N 3-ethoxy-1-phenylbutan-1-one Chemical compound CCOC(C)CC(=O)C1=CC=CC=C1 QANNWEQEHKZBDM-UHFFFAOYSA-N 0.000 description 1
- POKCGQXKNIJLCR-UHFFFAOYSA-N 4-methylcyclohex-3-en-1-one Chemical compound CC1=CCC(=O)CC1 POKCGQXKNIJLCR-UHFFFAOYSA-N 0.000 description 1
- WNZISGSGRPIJFX-UHFFFAOYSA-N 5-methylhex-4-en-3-one Chemical compound CCC(=O)C=C(C)C WNZISGSGRPIJFX-UHFFFAOYSA-N 0.000 description 1
- ZRSNZINYAWTAHE-UHFFFAOYSA-N Anisaldehyde Natural products COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 101700012268 Holin Proteins 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
- TWWSMHPNERSWRN-UHFFFAOYSA-N acetaldehyde diisopropyl acetal Natural products CC(C)OC(C)OC(C)C TWWSMHPNERSWRN-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002081 enamines Chemical class 0.000 description 1
- OSTREZKEFIGOHW-UHFFFAOYSA-N ethoxymethylcyclohexane Chemical compound CCOCC1CCCCC1 OSTREZKEFIGOHW-UHFFFAOYSA-N 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229940100595 phenylacetaldehyde Drugs 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Pyrane Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57111600A JPS595133A (ja) | 1982-06-30 | 1982-06-30 | β−アルコキシケトン類およびβ−ケトアセタ−ル類の製法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57111600A JPS595133A (ja) | 1982-06-30 | 1982-06-30 | β−アルコキシケトン類およびβ−ケトアセタ−ル類の製法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS595133A true JPS595133A (ja) | 1984-01-12 |
| JPH0155255B2 JPH0155255B2 (enrdf_load_stackoverflow) | 1989-11-22 |
Family
ID=14565460
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57111600A Granted JPS595133A (ja) | 1982-06-30 | 1982-06-30 | β−アルコキシケトン類およびβ−ケトアセタ−ル類の製法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS595133A (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61133233A (ja) * | 1984-11-29 | 1986-06-20 | ユニオン・キヤンプ・コ−ポレイシヨン | 新規なポリアミド |
-
1982
- 1982-06-30 JP JP57111600A patent/JPS595133A/ja active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61133233A (ja) * | 1984-11-29 | 1986-06-20 | ユニオン・キヤンプ・コ−ポレイシヨン | 新規なポリアミド |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0155255B2 (enrdf_load_stackoverflow) | 1989-11-22 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPS595133A (ja) | β−アルコキシケトン類およびβ−ケトアセタ−ル類の製法 | |
| JPH1135969A (ja) | 香料組成物 | |
| Hoffmann et al. | On the Constitutional Stability of η1‐Allylmetal Compounds | |
| JPS6314691B2 (enrdf_load_stackoverflow) | ||
| JP2867847B2 (ja) | ５−メチレン−１，３−ジオキソラン−４−オン類の製造方法 | |
| JP4540197B2 (ja) | （ｅ）−３−メチル−２−シクロペンタデセノンの製造法 | |
| US20060030719A1 (en) | Cis-3,5-disubstituted-dihydro-furan-2-ones and the preparation and use thereof | |
| JP2630470B2 (ja) | ２―シクロヘキシルプロピルアセテートを含有する香料組成物 | |
| JP2000053675A (ja) | 大環状ラクトン化合物、その製造法及び該化合物を含有する香料組成物 | |
| JPS6233231B2 (enrdf_load_stackoverflow) | ||
| JP3777407B2 (ja) | カルボン酸誘導体の製造法 | |
| JPH03501125A (ja) | α‐アセチル桂皮酸類又はそのエステル類のアルキレン及びジアルキルケタール類並びにアルキルα‐エノールエーテル類の製造方法 | |
| JPH0597749A (ja) | α−（２，４，４−トリメチルヘプチル又はヘプテニル−３−オキシ）−β−アルカノール及び該化合物を含有する香料組成物 | |
| JP4448346B2 (ja) | 新規な光学活性含フッ素環状化合物及びその製造方法 | |
| JPS62270572A (ja) | ３−置換メチル−６−エチル−５−オキサトリシクロ〔４・２・１・０ ↑３，↑７〕ノナン及びこれを含有する香料組成物 | |
| JP6047884B2 (ja) | 化合物 | |
| JPH05230075A (ja) | α−位にジフルオロメチル基を有するアルコ−ル誘導体の製造方法 | |
| JP4243397B2 (ja) | 新規な不飽和２級アルコールおよびその製造法 | |
| JP2848937B2 (ja) | 置換メチレンシクロペンタン類の製造法 | |
| PL172847B1 (pl) | Sposób wytwarzania nowego (E)-3,7!7-trimetylo-4-okten-1-olu | |
| JP6268551B2 (ja) | シクロプロパン環を有する化合物およびその香料組成物 | |
| JP4022413B2 (ja) | パーフルオロアルキルアクリル酸多量体および多量体組成物ならびにそれらの製造方法 | |
| JPH075491B2 (ja) | ジエノ−ル及びそのエステル、並びにそれらの製造方法 | |
| JPS60178838A (ja) | β−ヒドロキシカルボニル化合物類の製法 | |
| JPS6115853A (ja) | ２−置換−５−メチル−４−ヘキセン−１−アールの製造方法 |