Sulfuric Acid → Cyclopentanone, 2-(1-hydroxypentyl)-

Participants

Reaction Conditions

Reaction Steps

Valeraldehyde having an acid value of 3.4 mg-KOH/g was used as the starting material. 117.6 g (1.4 mol) cyclopentanone, 125.2 g water and 2.8 g (0.033 mol) 48% NaOH were introduced into a 500-mL four-necked flask, then the mixture was cooled to 0° C. under stirring, and 72.4 g (0.84 mol) valeraldehyde was added dropwise at the same temperature over 4 hours. Thereafter, the mixture was stirred at the same temperature for 4 hours. After the reaction was finished, the mixture was neutralized with 17.4 g of 10% sulfuric acid and the organic layer was analyzed by gas chromatography. In this analysis, a methyl silicon column was used and diethylene glycol monoethyl ether (carbitol) was added as the standard. The result indicated that the reaction mixture contained 124.4 g (0.73 mol) 2-(1-hydroxy-n-pentyl)cyclopentanone (yield 87.4%) and 2.5 g (0.016 mol) 2-pentylidene cyclopentanone.

Provenance & Evidence