GB1331204A - Alpha-methyl- butyric acid ester - Google Patents
Alpha-methyl- butyric acid esterInfo
- Publication number
- GB1331204A GB1331204A GB882572A GB882572A GB1331204A GB 1331204 A GB1331204 A GB 1331204A GB 882572 A GB882572 A GB 882572A GB 882572 A GB882572 A GB 882572A GB 1331204 A GB1331204 A GB 1331204A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methyl
- ethyl
- penten
- butyric acid
- acid
- 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
- WLAMNBDJUVNPJU-UHFFFAOYSA-N 2-methylbutyric acid Chemical compound CCC(C)C(O)=O WLAMNBDJUVNPJU-UHFFFAOYSA-N 0.000 title abstract 3
- UAXOELSVPTZZQG-UHFFFAOYSA-N tiglic acid Natural products CC(C)=C(C)C(O)=O UAXOELSVPTZZQG-UHFFFAOYSA-N 0.000 title abstract 2
- QUPRMGWZSNTJJX-UHFFFAOYSA-N 3-ethylpent-1-en-3-ol Chemical compound CCC(O)(CC)C=C QUPRMGWZSNTJJX-UHFFFAOYSA-N 0.000 abstract 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 abstract 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- -1 3-ethyl-1-pentyne-3-yl α-methyl-butyrate Chemical compound 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- ACIAHEMYLLBZOI-ZZXKWVIFSA-N Unsaturated alcohol Chemical compound CC\C(CO)=C/C ACIAHEMYLLBZOI-ZZXKWVIFSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000008065 acid anhydrides Chemical class 0.000 abstract 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 abstract 1
- 239000006227 byproduct Substances 0.000 abstract 1
- 229910000019 calcium carbonate Inorganic materials 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 230000032050 esterification Effects 0.000 abstract 1
- 238000005886 esterification reaction Methods 0.000 abstract 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 abstract 1
- 239000003205 fragrance Substances 0.000 abstract 1
- 238000005984 hydrogenation reaction Methods 0.000 abstract 1
- 229910052763 palladium Inorganic materials 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B9/00—Essential oils; Perfumes
- C11B9/0007—Aliphatic compounds
- C11B9/0015—Aliphatic compounds containing oxygen as the only heteroatom
- C11B9/0019—Aliphatic compounds containing oxygen as the only heteroatom carbocylic acids; Salts or esters thereof
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/14—Preparation of carboxylic acid esters from carboxylic acid halides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
- C07C69/22—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen having three or more carbon atoms in the acid moiety
- C07C69/24—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen having three or more carbon atoms in the acid moiety esterified with monohydroxylic compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fats And Perfumes (AREA)
Abstract
1331204 Methyl butyric acid esters L GIVAUDAN & CIE SA 25 Feb 1972 [26 Feb 1971] 8825/72 Heading C2C [Also in Division A5] The compound 3-ethyl-1-penten-3-yl a-methyl butyrate is prepared by (a) esterifying 3-ethyl- 1-penten-3-ol with α-methylbutyric acid or (b) partially hydrogenating 3-ethyl-1-pentyne-3-yl α-methyl-butyrate. The esterification may be with an acid or acid anhydride or chloride in a solvent at reflux temperature. The partial hydrogenation may be in the presence of a 5% palladium or calcium carbonate catalyst in the presence or absence of solvent. The alcohol may be prepared from dimethyl ketone condensed with acetylene to form an acetylenically unsaturated alcohol which may be esterified or partially hydrogenated. The product, particularly that containing 3-ethyl-1-penten-3-ol 1 by product is used as an odorant.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH289671A CH551361A (en) | 1971-02-26 | 1971-02-26 | PROCESS FOR MANUFACTURING A NEW (ALPHA) METHYL BUTTERIC ACID ESTER. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1331204A true GB1331204A (en) | 1973-09-26 |
Family
ID=4244030
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB882572A Expired GB1331204A (en) | 1971-02-26 | 1972-02-25 | Alpha-methyl- butyric acid ester |
Country Status (9)
| Country | Link |
|---|---|
| BE (1) | BE779849A (en) |
| BR (1) | BR7200980D0 (en) |
| CA (1) | CA928321A (en) |
| CH (1) | CH551361A (en) |
| DE (1) | DE2201365A1 (en) |
| FR (1) | FR2126441B1 (en) |
| GB (1) | GB1331204A (en) |
| IT (1) | IT948037B (en) |
| NL (1) | NL7200186A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3640233A1 (en) * | 2018-10-16 | 2020-04-22 | Basf Se | Ethers and esters of tertiary alkanols for use as aroma chemicals |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3225293A1 (en) * | 1982-07-07 | 1984-01-12 | Henkel KGaA, 4000 Düsseldorf | 2-METHYL PENTANIC ACID ESTER WITH BRANCHED OR CARBOCYCLIC ALCOHOL RESIDUE, THEIR PRODUCTION AND USE AS A FRAGRANCE |
| DE3429720A1 (en) * | 1984-08-13 | 1986-02-20 | Henkel KGaA, 4000 Düsseldorf | Smell |
-
1971
- 1971-02-26 CH CH289671A patent/CH551361A/en not_active IP Right Cessation
-
1972
- 1972-01-06 NL NL7200186A patent/NL7200186A/xx unknown
- 1972-01-12 DE DE19722201365 patent/DE2201365A1/en active Pending
- 1972-01-22 IT IT19729/72A patent/IT948037B/en active
- 1972-02-23 BR BR980/72A patent/BR7200980D0/en unknown
- 1972-02-24 CA CA135439A patent/CA928321A/en not_active Expired
- 1972-02-25 FR FR7206563A patent/FR2126441B1/fr not_active Expired
- 1972-02-25 BE BE779849A patent/BE779849A/en unknown
- 1972-02-25 GB GB882572A patent/GB1331204A/en not_active Expired
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3640233A1 (en) * | 2018-10-16 | 2020-04-22 | Basf Se | Ethers and esters of tertiary alkanols for use as aroma chemicals |
| WO2020079011A1 (en) | 2018-10-16 | 2020-04-23 | Basf Se | Ethers and esters of tertiary alkanols for use as aroma chemicals |
| CN112867703A (en) * | 2018-10-16 | 2021-05-28 | 巴斯夫欧洲公司 | Ethers and esters of tertiary alkanols as fragrance chemicals |
| JP2022504929A (en) * | 2018-10-16 | 2022-01-13 | ビーエーエスエフ ソシエタス・ヨーロピア | Ethers and esters of tertiary alkanols for use as fragrances |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2201365A1 (en) | 1972-09-07 |
| CH551361A (en) | 1974-07-15 |
| CA928321A (en) | 1973-06-12 |
| IT948037B (en) | 1973-05-30 |
| FR2126441B1 (en) | 1975-10-24 |
| NL7200186A (en) | 1972-08-29 |
| BE779849A (en) | 1972-08-25 |
| FR2126441A1 (en) | 1972-10-06 |
| BR7200980D0 (en) | 1973-05-24 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |