6-tert-butyl-1-benzofuran-5-ol

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 0.07 g of 6-t-butyl-5-hydroxybenzofuran was dissolved in 5 ml of acetic acid and a catalytic amount of 10% palladium on carbon was added. The mixture was stirred under a hydrogen pressure (3.5 kg/cm2) for 6 hours. After the palladium on carbon was filtered off, the solution was concentrated and the concentrate was purified by silica gel column chromatography (in n-hexane containing 9% ethyl acetate) to give 0.05 g of 6-t-butyl-5-hydroxy-2,3-dihydrobenzofuran as a white solid (yield 71%). After the palladium on carbon was filtered off the solution was concentrated the concentrate was purified by silica gel column chromatography (in n-hexane containing 9% ethyl acetate)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Under a nitrogen stream, 0.12 g of 6-t-butyl-5-trimethylacetoxybenzofuran was dissolved in 5 ml of n-hexane at room temperature and 1.31 ml of diisobutylaluminium hydride (1M in n-hexane) was added dropwise and the mixture was stirred overnight. After the reaction was quenched with 5% hydrochloric acid, the mixture was extracted with water and ethyl acetate. The organic layers were washed with saturated brine, dried over anhydrous magnesium sulfate and then concentrated. The concentrate was purified on a short column of silica gel (in n-hexane containing 5% ethyl acetate) to give 0.07 g of 6-t-butyl-5-hydroxybenzofuran as a reddish brown oil. After the reaction was quenched with 5% hydrochloric acid the mixture was extracted with water and ethyl acetate The organic layers were washed with saturated brine dried over anhydrous magnesium sulfate concentrated The concentrate was purified on a short column of silica gel (in n-hexane containing 5% ethyl acetate)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 0.07 g of 6-t-butyl-5-hydroxybenzofuran was dissolved in 5 ml of acetic acid and a catalytic amount of 10% palladium on carbon was added. The mixture was stirred under a hydrogen pressure (3.5 kg/cm2) for 6 hours. After the palladium on carbon was filtered off, the solution was concentrated and the concentrate was purified by silica gel column chromatography (in n-hexane containing 9% ethyl acetate) to give 0.05 g of 6-t-butyl-5-hydroxy-2,3-dihydrobenzofuran as a white solid (yield 71%). After the palladium on carbon was filtered off the solution was concentrated the concentrate was purified by silica gel column chromatography (in n-hexane containing 9% ethyl acetate)