Water → HCID 86737921, compound

Participants

Reaction Steps

Add 23.79 gm. (0.0655 mole) of 5-bromo-α-(3-isopropylphenoxy)-o-toluate to a solution of 5.24 gm. (0.1310 mole) of sodium hydroxide in 35 ml. of water and 315 ml. of methanol. Heat at reflux for 3 hours. Remove the methanol under vacuum and dilute the residual solution with 300 ml. of water. Extract with ether. Separate the aqueous layer and acidify with concentrated hydrochloric acid to the Congo Red end point. Extract the resulting oil into ether, wash with water and dry over magnesium sulfate. Remove the solvent under vacuum and allow the resulting oil (21.33 gm.) to stand overnight. Wash the solids formed with petroleum ether to obtain the title compound [yield 10.94 gm., m.p. 103°-122° C., pmr (CDCl3) 1.20(6H,d,(CH3)2CH--), 2.82(1H,m, (CH3)2CH--), 5.47(2H,s,CH2O--), 9.18 (1H, broad s, COOH)].

Provenance & Evidence