Synthesis of Carboxylic Acids, Esters, Alcohols and Ethers Containing a Tetrahydropyran Ring Derived from 6-Methyl-5-hepten-2-one
Hanzawa, Y; Hashimoto, K; Kasashima, Y; Takahashi, Y; Mino, T; Sakamoto, M; Fujita, T
| HERO ID | 1447546 |
|---|---|
| In Press | No |
| Year | 2012 |
| Title | Synthesis of Carboxylic Acids, Esters, Alcohols and Ethers Containing a Tetrahydropyran Ring Derived from 6-Methyl-5-hepten-2-one |
| Authors | Hanzawa, Y; Hashimoto, K; Kasashima, Y; Takahashi, Y; Mino, T; Sakamoto, M; Fujita, T |
| Journal | Journal of Oleo Science |
| Volume | 61 |
| Issue | 11 |
| Page Numbers | 631-640 |
| Abstract | 3-hydroxy acids, 3-hydroxy-3,7-dimethyloct-6-enoic acid (1) and 3-hydroxy-2,2,3,7-tetramethyloct-6-enoic acid (2), were prepared from 6-methyl-5-hepten-2-one, and they were subsequently used to prepare (2,6,6-trimethyltetrahydropyran-2-ypacetic acid (3) and 2-methy1-2-(2,6,6-trimethyltetrahydropyran-2-yl)propanoic acid (4), respectively, via cyclization with an acidic catalyst such as boron trifluoride diethyl etherate or iodine. The reaction of carboxylic acids 3 and 4 with alcohols, including methanol, ethanol, and 1-propanol, produced the corresponding methyl, ethyl, and propyl esters, which all contained a tetrahydropyran ring. Reduction of carboxylic acids 3 and 4 afforded the corresponding alcohols. Subsequent reactions of these alcohols with several acyl chlorides produced novel esters. The alcohols also reacted with methyl iodide and sodium hydride to provide novel ethers. A one-pot cyclization esterification of 1 to produce esters containing a tetrahydropyran ring, using iodine as a catalyst, was also investigated. |
| Doi | 10.5650/jos.61.631 |
| Pmid | 23138252 |
| Wosid | WOS:000310861500004 |
| Is Certified Translation | No |
| Dupe Override | No |
| Comments | Source: Web of Science WOS:000310861500004 |
| Is Public | Yes |
| Language Text | English |
| Keyword | tetrahydropyran ring; cyclization; esterification |