[I:1][C:2]1[C:3]([O:22][CH3:23])=[CH:4][C:5]([CH:19]([CH3:21])[CH3:20])=[C:6]([O:8]S(C2C=CC(C)=CC=2)(=O)=O)[CH:7]=1.[OH-].[K+].Cl.CCCCCC>C(O)(C)(C)C.O>[I:1][C:2]1[C:3]([O:22][CH3:23])=[CH:4][C:5]([CH:19]([CH3:21])[CH3:20])=[C:6]([OH:8])[CH:7]=1
To a mixture of 292 grams of toluene-4-sulfonic acid 5-iodo-2-isopropyl-4-methoxy-phenyl ester (0.66 Moles) in 600 mL tert-butyl alcohol was gradually added a solution of 90 g KOH in 400 mL water, and the resultant mixture was stirred overnight at 82 degrees C. The reaction mixture was neutralized with conc. HCl to a pH of 5-6, and then partitioned between 600 mL ethyl acetate and 400 mL water. The organic phase was dried over sodium sulfate, filtered and stripped under vacuum at 65 degrees C. to give a resinous liquid. Hexane (700 mL) was then added and the mixture heated to reflux. The liquid phase was decanted into another flask and stirred overnight at room temperature, during which time a white solid precipitated. The solid was isolated by filtration and vacuum dried to give 162 g of 5-iodo-2-isopropyl-4-methoxy-phenol, representing a yield of 82%: MS (M+H)=293.
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