Benzyl 2-benzyloxy-3-isopropylbenzoate → 2-Benzyloxy-3-isopropylbenzylalcohol

Participants

Reaction Steps

A solution of LiAlH4 (1M in THF, 8.13 ml) was added to freshly distilled THF (10 ml) 10 ml. A solution of benzyl 2-benzyloxy-3-isopropylbenzoate (2.27 g, 6.31 mmole) in THF (10 ml) was added via a syringe to the LiAlH4 solution. The temperature was maintain below 40° C. using a water bath and the reaction mixture stirred at ambient temperature overnight. The reaction was quenched with water and the pH adjusted to ~7 with dilute HCl. The resultant precipitate was filtered off and the filtrate partitioned between ethyl acetate/H2O. The organic phase was dried (MgSO4), evaporated and the residue purified by chromatography (eluant: ethyl acetate/hexane) to give 2-benzyloxy-3-isopropylbenzylalcohol (1.38 g, 83%).

Provenance & Evidence