7-Tert-butyl-chroman-4-ol → 7-(Tert-butyl)chroman-4-one

Participants

Reaction Steps

7-tert-Butyl-chroman-4-ol (assumed 32.1 mmol) was taken up in dichloromethane (250 mL) and with stirring was added PCC (14.36 g, 2eq) portion-wise. After the addition was complete, the resulting mixture was stirred for about 3 hours by which time the reaction was complete by TLC analysis. About 250 mL of hexanes were added to the mixture and it was then filtered through a pad of celite and the filtrate was concentrated. Purification by column chromatography on silica gel eluting with a gradient of 2% ethyl acetate in hexanes to 10% ethyl acetate in hexanes afforded the title compound as an off-white solid (3.838 g) (M+H)+=205.

Provenance & Evidence