5,6,7,8-Tetrahydro-1-naphthalenecarboxylic acid → (5,6,7,8-Tetrahydronaphthalen-1-yl)methanol

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Reaction Steps

A solution of 20 mL (0.019 mol) of 1.0M LiAlH4 in Et2O was cooled to -78° C. and treated dropwise with a solution of 3.42 g (0.019 mol) of 5,6,7,8-tetrahydro-1-naphthoic acid in 20 mL THF. The solution was allowed to warm to room temperature and stirred overnight. The solution was cooled to 0° C. and decomposed with 40 mL of a 0.43M solution of KHSO4. The mixture was filtered through Celite and washed with EtOAc. The organic phase was washed with 1N HCl and saturated NaCl. Drying over MgSO4 and removal of the solvent under reduced pressure left 3.02 g (98% yield) of the product. The structure was confirmed by NMR spectroscopy.

Provenance & Evidence