Water → [3-Methoxy-5-(3-methoxypropoxy)phenyl]methanol

HRID 1698356Notes

Reaction equation

HRID 1698356 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[C:8]([O:10][CH2:11][CH2:12][CH2:13][O:14][CH3:15])[CH:7]=[C:6]([O:16][CH3:17])[CH:5]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].O>C1COCC1>[CH3:17][O:16][C:6]1[CH:5]=[C:4]([CH2:3][OH:2])[CH:9]=[C:8]([O:10][CH2:11][CH2:12][CH2:13][O:14][CH3:15])[CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 59817706Methyl 3-methoxy-5-(3-methoxypropoxy)benzoate

Product 1

HCID 59817758[3-Methoxy-5-(3-methoxypropoxy)phenyl]methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 3-Methoxy-5-(3-methoxy-propoxy)-benzoic acid methyl ester (5 g, 19.7 mmol) and LAH (528 mg, 20 mmol) in THF (110 mL) is stirred under N2 at 0° C. for 3 h. After adding H2O, the reaction mixture is extracted with EtOAc. The combined organic phases are washed with H2O, brine and dried (Na2SO4). Concentration under reduced pressure and silica gel flash chromatography give the title compound as colorless oil. MS: 227 [M+H]+; tR (HPLC, CombiScreen ODS-AM 50×4.6 mm; 5-100% CH3CN+0.1% TFA/H2O+0.1% TFA for 5 min then 100% CH3CN+0.1% TFA for 2 min, flow 2.0 ml/min): 2.85 min.

Workup

  1. extractionthe reaction mixture is extracted with EtOAc
  2. washThe combined organic phases are washed with H2O, brine
  3. dry with materialdried (Na2SO4)
  4. concentrationConcentration under reduced pressure and silica gel flash chromatography

Sources & evidence

ORD record
ord-52da24d321874a4fb2e4b5e5f5e49fea
Source dataset
uspto-grants-2012_04
Patent number
US08163773B2

Reaction notes

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