4-Iodobenzoic acid → 4-Iodobenzyl alcohol
Reaction equation
[I:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[CH:4][CH:3]=1.CSC.B>O1CCCC1>[I:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][OH:7])=[CH:4][CH:3]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 4-iodobenzoic acid (22 g) in tetrahydrofuran (450 mL) was added borane dimethylsulfide complex (35.5 mL, 10M in tetrahydrofuran), and the solution was allowed to stir overnight. The reaction was quenched by addition of methanol, and the solvent was evaporated. The residue was dissolved in ethyl acetate and filtered. The solvent was evaporated to give a solid, which was recrystallized from ether to yield a white solid, which was chromatographed, eluting with ether, to give 4-iodobenzyl alcohol (15.1 g).
Workup
- customThe reaction was quenched by addition of methanol
- customthe solvent was evaporated
- dissolutionThe residue was dissolved in ethyl acetate
- filtrationfiltered
- customThe solvent was evaporated
- customto give a solid, which
- customwas recrystallized from ether
- customto yield a white solid, which
- customwas chromatographed
- washeluting with ether
Sources & evidence
- ORD record
- ord-8417a828e093485ab4902c3aaad9d943
- Source dataset
- uspto-grants-1996_05
- Patent number
- US05521179
Reaction notes
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