Isobutyraldehyde → 1-(4-Bromophenyl)-2-methylpropan-1-ol

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([Mg]Br)=[CH:4][CH:3]=1.[CH:10](=[O:14])[CH:11]([CH3:13])[CH3:12]>CCOCC>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:10]([OH:14])[CH:11]([CH3:13])[CH3:12])=[CH:4][CH:3]=1

Participants

Procedure

A solution of 4-bromophenylmagnesium bromide in ether was treated with isobutyraldehyde to give 1-(4-bromophenyl)-2-methylpropan-1-ol, b.p. 152°-154°C./15mm. This was dehydrated with polyphosphoric acid at 20°C., to give 1-bromo-4-(2-methyl-1-propenyl)benzene, b.p. 110°-112°C./6mm, which was hydrogenated in an ether/ethanol solvent containing 50% hydrobromic acid (2% by volume of solvent) over platinum oxide to give the desired product, b.p. 120°-122°C./22mm.