Hydrochloric Acid → HCID 22596842, compound

Participants

Reaction Conditions

Reaction Steps

A solution of ethyl 4-[3-hexyl-3-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-ureido]-benzoate (19) (296 mg, 0.62 mmole) in 8 mL ethanol was treated with 694 mg of potassium hydroxide in 3 mL water. THF (2 mL) was added and the mixture was heated to 45° C. for two hours. The reaction mixture was diluted with 10 mL water and the pH adjusted to 2 with concentrated HCl and then extracted with three 25 mL portions of ethyl acetate. The combined organic extracts were dried over MgSO4, filtered and concentrated in vacuo to provide a pale yellow solid. The product was purified by trituration in pentane and 231 mg (83%) of 4-[3-hexyl-3-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-ureido]-benzoic acid (13) were obtained as a pale yellow solid. M.P.: 176.6-177.1° C.

Provenance & Evidence