Water → 3-Methoxy-5-(phenylmethoxy)benzenemethanol

HRID 709674Notes

Reaction equation

HRID 709674 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:16]=[C:17]([O:19][CH3:20])[CH:18]=1)[C:12](OC)=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>C1COCC1>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH2:12][OH:13])[CH:16]=[C:17]([O:19][CH3:20])[CH:18]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 12658782Methyl 3-(benzyloxy)-5-methoxybenzoateHCID 21226445Aluminium lithium hydride

Product 1

HCID 696443123-Methoxy-5-(phenylmethoxy)benzenemethanolYield 93.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 3-(benzyloxy)-5-methoxybenzoate (8.90 g) in THF (100 mL) was added lithium aluminum hydride (1.30 g) at 0° C., and the mixture was stirred at room temperature for 1 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give the title compound (7.50 g) as an oil. This compound was used for the next step without further purification.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-08fd2742a2c1470b92d8bc78d3ffd12f
Source dataset
uspto-grants-2015_11
Patent number
US09181186B2

Reaction notes

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