Lithium borohydride → 2-Hydroxy-4-(hydroxymethyl)benzonitrile

Participants

Reaction Steps

Methyl 4-cyano-3-hydroxybenzoate (as described in Example 4, Step C) (0.50 g, 2.82 mmol) was dissolved in dry THF (30 mL), treated with LiBH4 (2.0M solution in THF) (5.64 mL, 11.28 mmol) and heated at reflux overnight. The reaction mixture was concentrated, then partitioned between EtOAc (50 mL) and 1N HCl (50 mL), the aqueous layer extracted with additional EtOAc (2×50 mL), the organic layers combined, washed with brine, and dried (MgSO4). Filtration and concentration to dryness gave the title compound.

Provenance & Evidence