Methanol → 2-Phenoxybenzyl alcohol

HRID 397818Notes

Reaction equation

HRID 397818 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C[O:8][C:9](=O)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.CO.S([O-])([O-])(=O)=O.[Mg+2]>C1COCC1>[O:16]([C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[CH2:9][OH:8])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 24083Sulfuric acid magnesium salt (1:1)HCID 607606Methyl 2-phenoxybenzoateHCID 21226445Aluminium lithium hydride

Product 1

HCID 36601112-Phenoxybenzyl alcoholYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A 1.0 M solution of lithium aluminum hydride in THF (25 ml, 25 mmol) was added to a solution of crude 2-phenoxybenzoic acid methyl ester (5.23 g, 22.9 mmol) in THF. The reaction mixture was stirred for 2.5 hours at room temperature. Methanol (10 ml) was added carefully. THF (50 ml) was added. Magnesium sulphate was added. The solids were filtered off. The solvent was removed in vacuo. The crude product was purified by flash chromatography on silica (90 g), using ethyl acetate/heptane (1:1) as eluent, to give 4.08 g of 2-phenoxybenzylalcohol.

Workup

  1. filtrationThe solids were filtered off
  2. customThe solvent was removed in vacuo
  3. customThe crude product was purified by flash chromatography on silica (90 g)

Sources & evidence

ORD record
ord-b84ee4892e1e4c678588e206c767965f
Source dataset
uspto-grants-2003_08
Patent number
US06610721B2

Reaction notes

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