4-Chloro-3-methoxybenzoic acid → (4-Chloro-3-methoxyphenyl)methanol

HRID 742502Notes

Reaction equation

HRID 742502 reaction equation
B.C1COCC1.[CH3:7][O:8][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][C:17]=1[Cl:18])[C:12](O)=[O:13]>C1COCC1>[CH3:7][O:8][C:9]1[CH:10]=[C:11]([CH2:12][OH:13])[CH:15]=[CH:16][C:17]=1[Cl:18]

Participants

4

Reactant 2

HCID 20633784-Chloro-3-methoxybenzoic acidHCID 2723981Borane;tetrahydrofuran

Product 1

HCID 10910038(4-Chloro-3-methoxyphenyl)methanolYield 91.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 30.6 ml of BH3.THF was added a solution of 3-methoxy-4-chlorobenzoic acid (35 g, 0.187 mol) in 450 ml of THF, and the mixture was refluxed with stirring under argon for 3 hours. The mixture was quenched with THF/water (1:1,300 ml), concentrated in vacuo, and the residue was partitioned between methylene chloride/water. The organic layer was dried over sodium sulfate and concentrated in vacuo to afford 29.4 g (90%) of 3-methoxy-4-chlorophenylmethanol.

Workup

  1. temperaturethe mixture was refluxed
  2. customThe mixture was quenched with THF/water (1:1,300 ml)
  3. concentrationconcentrated in vacuo
  4. customthe residue was partitioned between methylene chloride/water
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-732f3656552f435980b6ad86ec7bf231
Source dataset
uspto-grants-1996_09
Patent number
US05554620

Reaction notes

Loading…