[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([CH3:13])([CH3:12])[OH:11])=[CH:4][CH:3]=1.[OH-].[Na+].Br[CH2:17][CH2:18][OH:19].[I-].[Na+]>O>[OH:19][CH2:18][CH2:17][O:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][C:10]([CH3:13])([CH3:12])[OH:11])=[CH:6][CH:7]=1To a suspension of 4-hydroxy-α,α-dimethylbenzenepropanol (15 g, 0.083 m) in water, was added a solution of sodium hydroxide (5 g, 0.125 m) in water (50 ml). 2-Bromoethanol (11.4 g, 0.091 m) and sodium iodide (6.3 g) were successively added and the solution stirred and heated under reflux for 3 hours. The reaction mixture was then diluted with more water and extracted with ethyl acetate. Evaporation of the ethyl acetate gave a cream solid (21.3 g).
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