Hydrochloric Acid → 3-Chloro-4-hydroxybenzyl alchol

HRID 911446Notes

Reaction equation

HRID 911446 reaction equation
CC(C[AlH]CC(C)C)C.[Cl:10][C:11]1[CH:12]=[C:13]([CH:18]=[CH:19][C:20]=1[OH:21])[C:14](OC)=[O:15].Cl>C1(C)C=CC=CC=1>[Cl:10][C:11]1[CH:12]=[C:13]([CH:18]=[CH:19][C:20]=1[OH:21])[CH2:14][OH:15]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14487Diisobutylaluminum hydrideHCID 77580Methyl 3-chloro-4-hydroxybenzoate

Product 1

HCID 2574563-Chloro-4-hydroxybenzyl alchol

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Add a solution of DIBAL-H in toluene (1.0 M, 35 mL) to a solution of methyl 3-chloro-4-hydroxybenzoate (1.9 g, 10 mmol) at 0° C. under nitrogen. Stir the reaction at 0° C. and gradually warm to ambient temperature overnight. Quench the reaction with slow addition of 0.1N aqueous HCl, add more acid to break the gel-like solid to two clear layers. Separate the organic layer, and extract the aqueous layer with EtOAc three times. Combine the organic layers, wash with brine, dry over Na2SO4, filter and concentrate to give a white solid. MS (ES−) m/z 157 (M−H)−.

Workup

  1. customthe reaction at 0° C.
  2. customQuench
  3. customthe reaction
  4. additionadd more acid
  5. customSeparate the organic layer
  6. extractionextract the aqueous layer with EtOAc three times
  7. washCombine the organic layers, wash with brine
  8. dry with materialdry over Na2SO4
  9. filtrationfilter
  10. concentrationconcentrate
  11. customto give a white solid

Sources & evidence

ORD record
ord-088128e025b7472ca00d83226fadbca9
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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