Sodium Hydroxide → (+/-)-{4-[2,4-Bis(methoxymethoxy)phenyl]cyclohexylidene}acetic acid

Participants

Reaction Conditions

Reaction Steps

To a round bottomed flask equipped with magnetic stirrer was added trimethylsilyidiethylphosphonoacetate (1.08 ml, 3.83 mmol) and anhydrous tetrahydrofuran (25 ml). The stirred solution was cooled to 0° C. and n-butyl lithium (1.80 ml, 3.83 mmol, 2.2M in cyclohexanes) was added dropwise, via syringe over 5 min. The reaction mixture was allowed to warm slowly to room temperature and stirred for 17 hr. 4-[(2,4-Bis(methoxymethoxy)phenyl)]cyclohexanone (750 mg, 2.55 mmol) was added via syringe as a solution in tetrahydrofuran (25 ml). After 2 hr stirring at room temperature, the reaction mixture was poured into a separating funnel containing aqueous sodium hydroxide solution (10 ml, 10% w/v). After extracting once with diethyl ether (10 ml), the aqueous layer was acidified by adding concentrated hydrochloric acid (10 ml), then extracted with diethyl ether (3×20 ml). The combined organic layers were washed with water (10 ml), dried over magnesium sulfate, filtered and concentrated in vacuo affording the title compound (422 mg, 52%) as an oil. δH(CDCl3) 1.86 (2H, m), 2.00-2.13 (4H, m), 2.42 (2H, m), 3.19 (1H, m), 3.48 (3H, s), 3.51 (3H, s), 5.14 (2H, s), 5.21 (2H, s), 5.71 (1H, s), 6.67 (1H, dd), 6.81 (1H, d), 7.05 (1H, d).

Provenance & Evidence