Sodium Hydroxide → HCID 178509872, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of cis-ethyl 3-(4-cyanobenzyloxy)cyclobutanecarboxylate (0.44 g, 1.70 mmol) in 1,4-dioxane (10 mL) was added aqueous NaOH (1 N, 2.0 mL). The reaction was stirred at about 25° C. for about 16 h. The reaction was partitioned between 10% aqueous AcOH (20 mL) and EtOAc (25 mL). The layers were separated and the aqueous layer was extracted with additional EtOAc (25 mL). The combined organic extracts were washed with brine (20 mL), dried over anhydrous Na2SO4, filtered then concd in vacuo to give cis-3-(4-cyanobenzyloxy)-cyclobutanecarboxylic acid (0.24 g, 60%): LC/MS (Table 1, Method b) Rt=1.67 min; MS m/z: 232 (M+H)+.

Provenance & Evidence