3-Chloro-5-methoxybenzoic acid → (3-Chloro-5-methoxyphenyl)methanol

HRID 1686398Notes

Reaction equation

HRID 1686398 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[CH:9]=[C:10]([CH:14]=[C:15]([O:17][CH3:18])[CH:16]=1)[C:11](O)=[O:12]>C1COCC1.Cl>[Cl:7][C:8]1[CH:9]=[C:10]([CH2:11][OH:12])[CH:14]=[C:15]([O:17][CH3:18])[CH:16]=1

Participants

5

Reactant 2

HCID 129093413-Chloro-5-methoxybenzoic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 12909342(3-Chloro-5-methoxyphenyl)methanolYield 101.5%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminium hydride (1M in THF, 8.76 ml) was added dropwise to a stirred solution of the product of step (i) (1.63 g) in THF (40 ml) and stirred for 2 h. The reaction was diluted with 2 M HCl and extracted with ethyl acetate. The organic layer was washed with aqueous sodium hydrogen carbonate, dried (MgSO4) and evaporated under reduced pressure to give the subtitle compound (1.53 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with aqueous sodium hydrogen carbonate
  3. dry with materialdried (MgSO4)
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-313491dc57df4c8b8525158585c47432
Source dataset
uspto-grants-2012_04
Patent number
US08148572B2

Reaction notes

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