Potassium Hydroxide → 4-phenyltetrahydro-2H-pyran-4-carboxylic acid

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Reaction Steps

Methyl 4-phenyl-tetrahydro-2H-pyran-4-carboxylate (15.4 g, 69.9 mmol) was dissolved in EtOH (100 mL). KOH (39.2 g, 699 mmol) was then added. The reaction mixture was then heated at reflux for 2 hours and then cooled to ambient temperature, diluted with 150 mL of diethyl ether, added to a separatory funnel, partitioned with water, washed 2 times with 50 mL of water, and separated. The aqueous layer was acidified to a pH of 2 with concentrated HCl and extracted with CHCl3 (3×100 mL), dried over Na2SO4, and concentrated in vacuo to give the title compound (11.58 g) as a light yellow solid. MS m/e=229 (M+Na)+.

Provenance & Evidence