4-Chlorosalicylic acid → 5-Chloro-2-(hydroxymethyl)phenol

HRID 878610Notes

Reaction equation

HRID 878610 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[C:4]([OH:11])[CH:3]=1>C1COCC1>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][OH:7])=[C:4]([OH:11])[CH:3]=1

Participants

3

Reactant 1

HCID 787824-Chlorosalicylic acid

Product 1

HCID 3271485-Chloro-2-(hydroxymethyl)phenolYield 63,058.699%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

BH3 (1M in THF, 359 mL) was added into a solution of 4-chloro-2-hydroxybenzoic acid (20.63 g, 0.12 mmol) in THF (40 mL) drop wise at 0° C. After which, the mixture was stirred at r.t. overnight. Extracted with EA twice, and washed the organic phase with brine and dried with anhydrous Na2SO4, concentrated to give the title compound (12 g, 63%). 1H NMR (400 MHz, DMSO-d6): δ 4.42 (2H, s), 4.97-5.06 (1H, m), 6.77 (1H, d, J=2.0 Hz), 6.82 (1H, dd, J=2.0 Hz, 8.0 Hz), 7.27 (1H, d, J=8.4 Hz), 9.85 (1H, s).

Workup

  1. extractionExtracted with EA twice
  2. washwashed the organic phase with brine
  3. dry with materialdried with anhydrous Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-f3b0e030bad94c45a127414a43df0d19
Source dataset
uspto-grants-2015_03
Patent number
US08987461B2

Reaction notes

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