Hydrochloric Acid → HCID 15124013, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-methyl-4-hydroxy-7-tert-butylbenzofuran-2-carboxylic acid (0.250 g, 1.0 mmol), quinoline (0.75 mL), and copper powder (0.064 g, 1.0 mmol) was heated to 210° C. until gas evolution ceased (about 10 minutes) and then poured into 2N HCl (15 mL). Carbon tetrachloride (15 mL) was added and the biphasic mixture was filtered through celite. The layers were separated and the aqueous layer extracted with an additional portion of carbon tetrachloride (15 mL). The combined extracts were dried (Na2SO4) and concentrated. Flash chromatography using 10% ethyl acetate in hexane as eluant afforded 3-methyl-4-hydroxy-7-tert-butylbenzofuran, compound 10a. Recrystallization from hexane provided analytically pure material. 1H NMR d 1.46 (9H, s), 2.43 (3H, s), 6.49 (1H, d, J=8 Hz), 6.98 (1H, d, J=8 Hz), 7.36 (1H, s).

Provenance & Evidence