Sodium Hydroxide → (+-)-trans4-Methylene-2-phenylcyclopentanoic acid

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl(+−)-trans-4-methylene-2-phenylcyclopentanoate prepared as in Example 20, Step A (28.4 g, 131 mmol) in methanol (400 mL) was added 5N sodium hydroxide (131 mL, 656 mmol). The reaction was heated at 65° C. for 1 h then cooled and concentrated. The residue was taken up diluted with water, acidified with 2M hydrochloric acid and extracted twice with methylene chloride. The organic layers were each washed with brine, dried over sodium sulfate, combined and concentrated in vacuo to give the crude title acid (27.2 g) which was used directly in Step B.

Provenance & Evidence