Sodium Hydroxide → HCID 87735178, compound

Participants

Reaction Steps

A solution of the diester of example 62 (10.5 g, 20.8 mmol) in methanol (100 mL) was cooled in an ice bath and was treated drop wise with a solution of sodium hydroxide (1N, 42 mL). Stirring was continued for 30 minutes and then for an additional 48 hours at room temperature. The methanol was evaporated in a rotary evaporator and the alkaline reaction mixture was diluted with water followed by extracting with ether. The pH was adjusted to 4 by the addition of HCl (2N) and the acidic solution was extracted several times with ethyl acetate. The combined organic extracts were washed with brine, dried over sodium sulfate, filtered and evaporated to give the desired product (10.2, 100%) as a white foam: 1H NMR (CDCl3, 400 MHz) 7.70 (d, 1H), 7.26-7.46 (m, 16H), 2.72-2.99 (m, 1H), 1.99-2.42 (m, 4H), 1.42 (s, 9H).

Provenance & Evidence