Formaldehyde → HCID 56991944, compound

Participants

Reaction Steps

3-[3,5-bis-(1,1-dimethylethyl)-4-hydroxyphenyl]-2-mercaptopropanoic acid (4.58 g; 14.75 mmole), prepared substantially in accordance with the method described in Example 1A, was suspended in 50 ml of toluene. Under a nitrogen atmosphere, 0.45 g (15.0 mmoles) of paraformaldehyde was added followed by 1.67 grams (15.56 mmoles) of benzylamine. The resulting solution was heated at reflux temperature for one hour with removal of water by means of a Dean-Stark apparatus. The solution was allowed to cool to room temperature. Fifty milliliters of ethyl acetate was added and the resultant clear, yellow solution was extracted with 35 ml of a 0.5N hydrochloric acid solution, resulting in a cloudy yellow organic layer. An additional 30 ml of ethyl acetate was added to the cloudy organic layer and the resulting solution was extracted again with 35 ml of a 0.5N hydrochloric acid solution, resulting in yet another cloudy organic layer. Fifteen milliliters of ethyl acetate was added to the cloudy organic layer which was then washed with 30 ml of a 1:1 bicarbonate/brine solution, followed by 30 ml of a brine solution. The resulting solution was then dried with sodium sulfate, filtered and evaporated to provide 7.2 g of a viscous, cloudy oil.

Provenance & Evidence