Benzenepropanoic acid, 3,5-bis(1,1-dimethylethyl)-4-hydroxy-, ethyl ester → gamma-Propanol

Participants

Reaction Steps

To a suspension lithium aluminum hydride (11.2 g) in diethyl ether (500 mL) is added over a period of 30 minutes ethyl 3-[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]propionate (60.0 g) in diethyl ether (100 mL). The mixture is heated at reflux for 3 hours and then quenched by the sequential addition of water (11 mL), 10% aqueous sodium hydroxide (11 mL) and water (66 mL). The resulting suspension is washed with tetrahydrofuran and the filtrate is concentrated to give 48 g of 3-[3,5-bis(1,1-dimethylethyl)-4-hydroxy-phenyl]propanol. Trituration of the residue with heptane gave 46 g of light yellow crystals. The 1H NMR spectrum and field desorption mass spectrum are consistent with the above-specified product.

Provenance & Evidence