3,5-Dichloro-4-hydroxybenzoic acid → Benzenemethanol, 3,5-dichloro-4-hydroxy-

HRID 1063872Notes

Reaction equation

HRID 1063872 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([Cl:12])[C:10]=1[OH:11])[C:5](O)=[O:6].B.C1COCC1>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:5][OH:6])[CH:8]=[C:9]([Cl:12])[C:10]=1[OH:11]

Participants

4

Reactant 2

HCID 187493,5-Dichloro-4-hydroxybenzoic acidHCID 2723981Borane;tetrahydrofuran

Product 1

HCID 176409Benzenemethanol, 3,5-dichloro-4-hydroxy-Yield 99.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 3,5-dichloro-4-hydroxybenzoic acid (4.0 g, 19.3 mmol) in THF (60 ml) under argon was added borane-THF complex (39.0 mmol, 39.0 ml of 1 M solution in THF) dropwise. After addition, the reaction mixture was heated at 60° C. for 6 h, then quenched with water and extracted with ethyl acetate three times. The organic extract was washed with water, then brine, dried (sodium sulfate) and concentrated in vacuo to afford the title compound (3.7 g, 99%) as white solid. 1H NMR (400 MHz, CDCl3) δ 7.28 (s, 2H), 5.83 (s, 1H), 4.59 (s, 2H), MS: (M+1-H2O)=175

Workup

  1. additionAfter addition
  2. customquenched with water
  3. extractionextracted with ethyl acetate three times
  4. extractionThe organic extract
  5. washwas washed with water
  6. dry with materialbrine, dried (sodium sulfate)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cc32e226d4524a23a27f31ed755d1149
Source dataset
uspto-grants-2005_11
Patent number
US06967220B2

Reaction notes

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