Aluminium lithium hydride → HCID 86723756, compound

Participants

Reaction Steps

To a suspension of LiAlH4 (1.90 g, 50.2 mmol) in dry THF (60 mL) was added dropwise methyl 5-bromo-2-methyl-3-(propan-2-yloxy)benzoate (Cpd PP, 17.0 g, 65.6 mmol) in THF (40 mL) at −5° C. After the addition, the resulting mixture was allowed to stir at room temperature for 1 hour. The reaction mixture was quenched with 20% NaOH (10 mL) at −5° C. and then stirred at room temperature for 30 minutes. The resulting mixture was filtered and the solids were washed with EtOAc (3×30 mL). The filtrate was concentrated under vacuum to give [5-bromo-2-methyl-3-(propan-2-yloxy)phenyl]methanol (108a, 8 g, 74%) as a yellow oil.

Provenance & Evidence