Acetate → Benzenemethanol,2-hydroxy-3,5-dimethyl-

Participants

Reaction Steps

75 g of NaOH were dissolved in 300 ml of deionized (DI) water. 183.3 g 2,4-dimethylphenol were added, and the mixture was cooled to 15°-20° C. 188 g of aqueous formaldehyde (made from 152g 37% formalin diluted with 36 g water) were added over half an hour, while the temperature was maintained below 20° C. After stirring overnight, Thin Layer Chromotography (TLC) in 2:1 hexane/ethyl. acetate showed a single spot, and no remaining 2,4-dimethylphenol. The pH was then adjusted to 6-7 with about 200 ml of 50% aqueous acetic acid. The mixture was transferred to a 2 liter beaker, and extracted with ethyl acetate (400 ml). Removal of the ethyl acetate in a vacuum gave 221.0 g (97.4%) of the desired product as a clear oil or a low-melting solid.

Provenance & Evidence