Ethyl 3-(1,1-dimethylethyl)-4-hydroxy-5-methylbenzenepropanoate → 75546-54-2

Participants

Reaction Steps

To a suspension lithium aluminum hydride (15.2 g) in tetrahydrofuran (500 mL) is added over a period of 60 minutes ethyl 3-[3-(1,1-dimethylethyl)-4-hydroxy-5-methylphenyl]propionate (80.0 g) in tetrahydrofuran (100 mL). The mixture is heated at reflux for 2 hours and then quenched by the sequential addition of water (17 mL), 10% aqueous sodium hydroxide (17 mL) and water (51 mL). The resulting suspension is washed with tetrahydrofuran and the filtrate is concentrated to give 40 g of crude 3-[3-(1,1-dimethylethyl)-4-hydroxy-5-methylphenyl]propanol. The crude intermediate is crystallized from heptane/toluene to give 38 g of light yellow crystals. The 1H NMR and field desorption spectra are consistent with the above-specified product.

Provenance & Evidence