Aluminium lithium hydride → (4-Chloro-3-methoxyphenyl)methanol

HRID 2104251Notes

Reaction equation

HRID 2104251 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([C:6](OC)=[O:7])=[CH:4][C:3]=1[O:12][CH3:13].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1.C(Cl)Cl>[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([CH2:6][OH:7])=[CH:4][C:3]=1[O:12][CH3:13]

Participants

5

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 44886974Methyl 4-chloro-3-methoxybenzoate

Product 1

HCID 10910038(4-Chloro-3-methoxyphenyl)methanol

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl 4-chloro-3-methoxybenzoate (5 g, 25 mmol, 1 equiv) in 15 mL of THF and 15 mL of DCM was cooled to 0° C. and treated with LiAlH4 (2.8 g, 3 equiv) overnight and was allowed to warm to rt. The reaction was then quenched with saturated sodium sulfate. Removal of the solid by filtration through celite followed by evaporation of the filtrate gave 4-chloro-3-methoxybenzyl alcohol.

Workup

  1. customThe reaction was then quenched with saturated sodium sulfate
  2. customRemoval of the solid
  3. filtrationby filtration through celite
  4. customfollowed by evaporation of the filtrate

Sources & evidence

ORD record
ord-d3bfbae39385437fa12f5bd6ec78c03d
Source dataset
uspto-grants-2009_08
Patent number
US07576218B2

Reaction notes

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