Lithium Hydroxide → 3-(4-Cyanotetrahydro-2H-pyran-4-yl)benzoic acid

Participants

Reaction Steps

To a solution of methyl 3-(4-cyanotetrahydro-2H-pyran-4-yl)benzoate 80 (1.3 g, 5.3 mmol) in (25 mL) of THF/MeOH/H2O (3/1/1) was added lithium hydroxide (419 mg, 17.5 mmol) in water (5 mL) and stirred overnight at rt. The reaction mixture was concentrated and extracted with CH2Cl2 to remove the excess of bis(2-chloroethyl)ether. The aqueous layer was then acidified with 2N HCl solution to (pH=1) and extracted with CH2Cl2. Organic layer was washed with brine and evaporated to give 3-(4-cyanotetrahydro-2H-pyran-4-yl)benzoic acid 81 (526 mg, 42%).

Provenance & Evidence