Acetic Acid → 2-Oxocyclohexaneheptanoic acid

Reaction equation

C([C:6]1([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([O-:21])=[O:20])[CH2:11][CH2:10][CH2:9][CH2:8][C:7]1=[O:12])(OCC)=O.S(=O)(=O)(O)O.C(O)(=O)C>O>[C:7]1(=[O:12])[CH2:8][CH2:9][CH2:10][CH2:11][CH:6]1[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([OH:21])=[O:20]

Participants

Procedure

A stirred mixture of 380 g. of mixed methyl and ethyl esters of 7-(2-carbethoxycyclohexan-1-on-2-yl)heptanoate (Example 10), 202 ml. of concentrated sulfuric acid, 970 ml. of glacial acetic acid, and 970 ml. of water is refluxed for 22.5 hours. The cooled reaction mixture is treated with 380 g. of sodium carbonate and 2 liters of water and is extracted with ether. Acidic material is partitioned from the ether extract with 1.0M sodium carbonate. The aqueous phase is acidified with concentrated hydrochloric acid and extracted with ether. The extract is washed successively with water and saturated sodium chloride, dried, and evaporated to give an oil.