[BH4-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:11]([CH:18]=[O:19])=[C:12]([CH3:17])[CH:13]=[C:14]([CH3:16])[CH:15]=2)=[CH:6][C:5]=1[CH3:20].[Cl-].[NH4+]>C(O)C>[F:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[C:14]([CH3:16])[CH:13]=[C:12]([CH3:17])[C:11]=2[CH2:18][OH:19])=[CH:6][C:5]=1[CH3:20]Sodium borohydride (0.45 g, 12 mmoles) was added to a stirred suspension of 4'-fluoro-3,3',5-trimethyl-1,1'-biphenyl-2-carboxaldehyde (2.9 g, 12 mmoles) in ethanol (20 ml) which was cooled in an ice-water bath. After 5 minutes the cooling bath was removed and the reaction mixture was stirred at ambient temperature for one hour. The solution was cooled to 0° C. and excess ammonium chloride (2.67 g, 50 mmoles) was added and the mixture was partitioned between ether (150 ml) and water (50 ml). The water was separated and extracted with ether (50 ml). The combined ether extracts were washed with water (2×50 ml) dried (MgSO4), filtered, and the solvent evaporated in vacuo to leave the title compound, a gum which crystallized on standing, to give 2.77 g, m.p. 74°-75° C. A sublimed sample had m.p. 102°-103° C.
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