[Na].[H-].COCCO[Al+]OCCOC.[F:14][C:15]1[CH:30]=[CH:29][C:18]([O:19][C:20]2[CH:28]=[CH:27][CH:26]=[CH:25][C:21]=2[C:22](O)=[O:23])=[CH:17][CH:16]=1.[OH-].[Na+]>C1C=CC=CC=1>[F:14][C:15]1[CH:30]=[CH:29][C:18]([O:19][C:20]2[CH:28]=[CH:27][CH:26]=[CH:25][C:21]=2[CH2:22][OH:23])=[CH:17][CH:16]=136.1 ml of 70% sodium-bis-(2-methoxyethoxy) aluminum hydride in benzene are added dropwise over a one hour span to a stirring mixture of 15 g of 2-(4-fluorophenoxy)benzoic acid in 150 ml of benzene under nitrogen at ambient temperature. After total addition, the reaction mixture is stirred for an additional 30 minutes and then permitted to stand for 4 days. Thereafter, the reaction mixture is cooled to 0° C. before adding 100 mls of 10% sodium hydroxide while stirring. Following this addition, the layers separate and the aqueous layer is extracted twice with 100 ml portions of benzene. The combined benzene solutions are successively washed twice with 100 ml portions of water, washed once with 60 ml of saturated sodium chloride solution and dried, providing a clear yellow oil. The oil is distilled at 118.5°-121.5° C. and 0.07 mm pressure to provide the clear, colorless liquid, 2-(4-fluorophenoxy)benzyl alcohol.
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