Borane → 3-Iodo-4-methylbenzyl alcohol
Reaction equation
[I:1][C:2]1[C:10](C)=CC=C[C:3]=1[C:4](O)=O.B.[O:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1>>[I:1][C:2]1[CH:10]=[C:16]([CH2:17][OH:13])[CH:15]=[CH:14][C:3]=1[CH3:4]Participants
4
Procedure
To a solution of 5.0 g (19.1 mmol) of 2-iodo-3-methyl benzoic acid in 50 mL of anhydrous tetrahydrofuran, was slowly added 22 mL of a 1M borane solution in tetrahydrofuran. The resultant reaction mixture was reacted for approximately ninety minutes and then was quenched with ethanol resulting in the evolution of hydrogen gas. The mixture was diluted with ethyl acetate. The resulting layers were separated and the organic layer was washed sequentially with sodium bicarbonate and brine, dried over sodium sulfate, filtered and crystallized from a hexane/ethyl acetate mixture to provide 120 mg of the desired subtitled compound.