Hydrochloric Acid → 4-Chloro-3-(hydroxymethyl)phenol

HRID 657837

Reaction equation

HRID 657837 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][C:9]=1[C:10](O)=[O:11].Cl>O1CCCC1.O.O1CCCC1>[Cl:7][C:8]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][C:9]=1[CH2:10][OH:11]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 4582102-Chloro-5-hydroxybenzoic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 247215304-Chloro-3-(hydroxymethyl)phenol

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21881883Oxolane--water (1/1)Solvent

Procedure

Lithium aluminium hydride (1M in diethyl ether, 25 mL, 25 mmol) was added to an ice-cooled solution of 2-chloro-5-hydroxy-benzoic acid (4 g, 23.2 mmol) in tetrahydrofuran (200 mL) and the mixture was heated under reflux for 6 hours. The mixture was then diluted with a mixture of water/tetrahydrofuran, acidified with 1M hydrochloric acid, and extracted with ethyl acetate. The organic solution was dried over sodium sulphate and concentrated in vacuo to afford the title compound in quantitative yield, 4.3 g.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 6 hours
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic solution was dried over sodium sulphate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9d324e7d830b4262a401a8f0f3f35f71
Source dataset
uspto-grants-2011_12
Patent number
US08076356B2

Linked notes

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