Water → 3,4-Dimethoxyphenethyl alcohol

HRID 1059035Notes

Reaction equation

HRID 1059035 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][C:12](O)=[O:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].O>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][OH:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

4

Reactant 2

HCID 962WaterHCID 7139(3,4-Dimethoxyphenyl)acetic acid

Product 1

HCID 819113,4-Dimethoxyphenethyl alcohol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3,4-dimethoxyphenylacetic acid (2 g) in anhydrous THF (40 ml) at 0° C. under N2 was added dropwise borane-methyl sulfide complex (10 M, 1.5 ml). The mixture was stirred at room temperature for further 4 hrs. Cold water (5 ml) was added to destroy any excess of borane followed by the addition of H2SO4 (1 M, 50 ml). The mixture was extracted three time with ethyl acetate (50 ml). The organic layer was separated and evaporated off to give a colourless liquid which was then purified by column chromatography to afford a colourless solid in quantitative yield.

Workup

  1. customto destroy any excess of borane
  2. additionfollowed by the addition of H2SO4 (1 M, 50 ml)
  3. extractionThe mixture was extracted three time with ethyl acetate (50 ml)
  4. customThe organic layer was separated
  5. customevaporated off
  6. customto give a colourless liquid which
  7. customwas then purified by column chromatography
  8. customto afford a colourless solid in quantitative yield

Sources & evidence

ORD record
ord-4d449473bac44edd8d7e50e9077c3827
Source dataset
uspto-grants-2003_02
Patent number
US06518315B1

Reaction notes

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