[C:1]1([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]([OH:11])([CH3:10])[CH:8]=[CH2:9].[BH4-].[Na+].B(F)(F)F.[OH-:24].[Na+].OO>COCCOCCOC.O>[C:1]1([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]([OH:11])([CH3:10])[CH2:8][CH2:9][OH:24]
2.24 g. of 3-p-biphenylyl-1-buten-3-ol (obtainable from p-biphenylylmagnesium bromide and methyl vinyl ketone) are dissolved in 5 ml. of diglyme, 3 ml. of a 1 M solution of NaBH4 in diglyme are added and a solution of 0.56 g. of BF3 etherate in 1.2 ml. of diglyme is added dropwise under N2. 0.7 ml. of water is then added and 1.4 ml. of 3N NaOH and 1.4 ml. of 30% H2O2 are then added dropwise at 80°-100°. The mixture is cooled, treated with ice water, and standard working up gives 3-p-biphenylyl-1,3-butanediol, m.p. 115°-117° (the boric acid ester formed as an intermediate being hydrolyzed).
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