4-Iodobenzoic acid → 4-Iodobenzyl alcohol

HRID 441203

Reaction equation

HRID 441203 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]=1

Participants

4

Reactant 2

HCID 120854-Iodobenzoic acidHCID 12423031(Dimethyl sulfide)trihydroboron

Product 1

HCID 290124-Iodobenzyl alcoholYield 72.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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

  1. customThe reaction was quenched by addition of methanol
  2. customthe solvent was evaporated
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. filtrationfiltered
  5. customThe solvent was evaporated
  6. customto give a solid, which
  7. customwas recrystallized from ether
  8. customto yield a white solid, which
  9. customwas chromatographed
  10. washeluting with ether

Sources & evidence

ORD record
ord-8417a828e093485ab4902c3aaad9d943
Source dataset
uspto-grants-1996_05
Patent number
US05521179

Linked notes

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