[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9]O)=[CH:4][CH:3]=1.[OH-].[K+].[CH2:13](Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C1C[O:24][CH2:23][CH2:22]1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:13]([O:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][CH2:22][CH2:23][OH:24])=[CH:6][CH:7]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1In a 250 ml reaction flask 2-(4-Hydroxyphenyl)-ethanol of formula, (5) (10 g, 0.07246 mol), potassium hydroxide (6.1 g, 0.1087 mol) and catalytic amount of phase transfer catalyst tetrabutyl ammonium bromide (0.150 g) was disssolved in 65 ml of THF. Stirred it for 1.5 hr. Benzyl bromide (8.6 ml, 0.07246 mol), was added to the reaction mixture dropwise. Stirred the reaction mixture at room temperature for 4 hrs. The progress of reaction was cheked by TLC. Filtered the reaction mixture and concentrated the filtrate on rota-vapour. The crude product was recrystalised from petroleum ether to afford 4-benzyloxy-(2-phenethyl ethanol) of formula (7), 14.9 g (90%) mp 85–86° C.
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