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

HRID 514453

Reaction equation

HRID 514453 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-fb9b2566fa2442639839d8d0d4291d11
Source dataset
uspto-grants-2015_08
Patent number
US09107916B2

Linked notes

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