Hydrochloric Acid → HCID 15124014, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-methyl-4-hydroxy-5,7-di-tert-butylbenzofuran-2-carboxylic acid (0.350 g, 1.14 mmol), quinoline (1.0 mL), and copper powder (0.072 g 1.14 mmol) was heated to 210° C. until gas evolution had ceased. The mixture was cooled, diluted with ethyl acetate (30 mL) and poured into 2N HCl. The biphasic mixture was filtered through a celite pad and the layers separated. The aqueous layer was extracted with ethyl acetate (50 mL) and the combined organic layers dried (Na2SO4) and concentrated. Flash chromatography afforded 3-methyl-4-hydroxy-5,7-di-tert-butylbenzofuran, compound 10b. 1H NMR d 1.46 (9H, s), 1.49 (9H, s), 2.46 (3H, s), 5.12 (1H, s), 7.11 (1H, s), 7.29 (1H, s).

Provenance & Evidence