2,4,6-Trichlorobenzoic acid → 2,4,6-Trichlorobenzyl alcohol

HRID 1514913Notes

Reaction equation

HRID 1514913 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[C:7]([Cl:12])[C:3]=1[C:4](O)=[O:5]>C1COCC1>[Cl:1][C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[C:7]([Cl:12])[C:3]=1[CH2:4][OH:5]

Participants

3

Reactant 1

HCID 57642,4,6-Trichlorobenzoic acid

Product 1

HCID 45825742,4,6-Trichlorobenzyl alcohol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 2,4,6-trichlorobenzoic acid (451 mg, 2.0 mmol) in THF (15 mL) was added BH3 (3 mL of a 1M solution in THF). After the addition, the solution was refluxed overnight. The reaction was quenched with water and the aqueous layer was extracted with EtOAc. The organic layer was washed with water, brine, dried with MgSO4, and filtered. The solvent was removed under reduced pressure to give (2,4,6-trichlorophenyl)-methanol as a white solid.

Workup

  1. additionAfter the addition
  2. temperaturethe solution was refluxed overnight
  3. customThe reaction was quenched with water
  4. extractionthe aqueous layer was extracted with EtOAc
  5. washThe organic layer was washed with water, brine
  6. dry with materialdried with MgSO4
  7. filtrationfiltered
  8. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-a93825771a8e47688b41085fa8147d27
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

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