HCID 14923120, compound → HCID 14684983, compound

Participants

Reaction Steps

A 10% palladium carbon catalyst (250 mg) was added to a solution of the nitrophenol (316 mg, 1.62 mmol) in ethanol (20 ml) and stirred under hydrogen atmosphere at room temperature for 12 hours. The reaction solution was filtered off through celite and the filtrate was evaporated in vacuo to provide 260 mg (yield 97%) of 2-amino-6-tert-butylphenol as red crystals. Potassium O-ethyl dithiocarbonate (242 mg, 1.51 mmol) was added to a solution of the aminophenol (227 mg, 1.37 mmol) in ethanol (10 ml) followed by heating to reflux for eight hours. After allowing to cool, the solvent was evaporated in vacuo and the resulting residue was dissolved in water, acidified with concentrated hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with water and a saturated sodium chloride solution successively and dried over an hydrous sodium sulfate and the solvent was evaporated therefrom. The residue was purified by a silica gel column chromatography (20 g of silica gel; developing solvent, hexane:acetone=4:1) to provide 124 mg (yield 44%) of 7-tert-butyl-2-mercaptobenzooxazole as colorless crystals.

Provenance & Evidence