Sodium Hydroxide → 3-m-Anisyl-1-propanol

Participants

Reaction Conditions

Reaction Steps

3-(3-Methoxyphenyl)propionic acid (see Example 1, Step J) (10.09 g, 0.058 mol) dissolved in anhydrous THF 60 mL) was added dropwise to a solution of LiAlH4 (1M in THF) (60 mL, 0.06 mol) in THF (60 mL) at ambient temperature under Ar. The resulting solution was stirred at reflux for 6 hr, then cooled to 0° C., treated dropwise with H2O (2.2 mL), 20% NaOH (1.7 mL), then H2O (6.62 mL). After stirring for 15 min, MgSO4 was added, stirring was continued for 15 min, the solids were filtered off, washed well with EtOAc, and the filtrate concentrated to dryness to give the title compound. MS (M+1) 167.1

Provenance & Evidence