Formaldehyde → HCID 53660746, compound

Participants

Reaction Steps

3-[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]-2-mercaptopropanoic acid (2.0 g; 6.45 moles), prepared substantially in accordance with the method described in Example 1A, was suspended in 20 ml of toluene. Under a nitrogen atmosphere, 0.2 g (6.45 mmoles) of paraformaldehyde was added, followed by 1.18 g (6.45 moles) of aminodiphenylmethane. An additional 10 ml of toluene was added and the resulting solution was heated at reflux temperature for 70 minutes with removal of water by means of a Dean-Stark apparatus. The solution was allowed to cool, after which the toluene was distilled off until about 10 ml of a light, brown solution remained. Fifteen milliliters of hexanes were added and the resultant solution was partitioned between ethyl acetate and 1N hydrochloric acid. The organic layer was washed with a saturated sodium bicarbonate solution and a brine solution, dried with sodium sulfate, filtered, and evaporated to provide a foam. The crude product was purified by silica gel chromatography and evaporated under vacuum to provide 2.99 g of a yellow foam. mp 286°-287° C. (dec).

Provenance & Evidence