Methanol → 3-(3,5-DIMETHOXY-PHENYL)-PROPAN-1-OL

HRID 1511878Notes

Reaction equation

HRID 1511878 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][C:13](O)=[O:14])[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.CO>C1COCC1>[CH3:10][O:9][C:7]1[CH:6]=[C:5]([CH2:11][CH2:12][CH2:13][OH:14])[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=1

Participants

4

Reactant 2

HCID 887Methanol2×HCID 38702163-(3,5-dimethoxyphenyl)propanoic Acid

Product 1

HCID 113330533-(3,5-DIMETHOXY-PHENYL)-PROPAN-1-OL

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-(3,5-dimethoxyphenyl)propanoic acid (2.00 g, 9.51 mmol) in THF (2.0 mL) was added dropwise to a stirred solution of borane-tetrahydrofuran complex (20.93 mL, 20.93 mmol) so as to maintain reaction temperature below 35° C. The mixture was allowed to stir overnight at room temperature. Methanol was added dropwise to the stirred mixture until visible reaction had ceased. An additional 20 mL of methanol was added and the reaction was stirred for 4 hours. The crude mixture was concentrated, filtered and purified by silica gel chromatography (1:1 heptane:EtOAc as eluant). Fractions containing product were combined and concentrated to give 3-(3,5-dimethoxy-phenyl)-propan-1-ol as an oil.

Workup

  1. temperatureto maintain
  2. customreaction temperature below 35° C
  3. stirringthe reaction was stirred for 4 hours
  4. concentrationThe crude mixture was concentrated
  5. filtrationfiltered
  6. custompurified by silica gel chromatography (1:1 heptane:EtOAc as eluant)
  7. additionFractions containing product
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-562603a355814896a88dde69ba9765d3
Source dataset
uspto-grants-2012_07
Patent number
US08217027B2

Reaction notes

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