Borane → 3-Iodo-4-methylbenzyl alcohol

HRID 400271Notes

Reaction equation

HRID 400271 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

Reactant 3

HCID 6331BoraneHCID 8028Tetrahydrofuran2×HCID 27593652-Iodo-3-methylbenzoic acid

Product 1

HCID 51667983-Iodo-4-methylbenzyl alcohol

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.

Workup

  1. customThe resultant reaction mixture
  2. customwas reacted for approximately ninety minutes
  3. customwas quenched with ethanol resulting in the evolution of hydrogen gas
  4. additionThe mixture was diluted with ethyl acetate
  5. customThe resulting layers were separated
  6. washthe organic layer was washed sequentially with sodium bicarbonate and brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. customcrystallized from a hexane/ethyl acetate mixture

Sources & evidence

ORD record
ord-38ef0b3b8b91463b90ac2509a170e0b0
Source dataset
uspto-grants-1998_10
Patent number
US05827891

Reaction notes

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