Water → Methyl 4-(hydroxymethyl)cinnamate

HRID 618762Notes

Reaction equation

HRID 618762 reaction equation
[CH:1]([C:3]1[CH:14]=[CH:13][C:6]([CH:7]=[CH:8][C:9]([O:11][CH3:12])=[O:10])=[CH:5][CH:4]=1)=[O:2].[BH4-].[Na+].O>CO>[OH:2][CH2:1][C:3]1[CH:4]=[CH:5][C:6]([CH:7]=[CH:8][C:9]([O:11][CH3:12])=[O:10])=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 53401287Methyl 3-(4-formylphenyl)-2-propenoate

Product 1

HCID 54313853Methyl 4-(hydroxymethyl)cinnamateYield 93.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 4-formylcinnamate (5.58 g) in methanol (100 ml) was added sodium borohydride (0.4 g), and the mixture was stirred at room temperature for an hour. The reaction mixture was poured into water and extracted with methylene chloride. The methylene chloride layer was washed with a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. Evaporation of the solvent under reduced pressure gave methyl 4-(hydroxymethyl)cinnamate (5.27 g).

Workup

  1. extractionextracted with methylene chloride
  2. washThe methylene chloride layer was washed with a saturated aqueous sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customEvaporation of the solvent under reduced pressure

Sources & evidence

ORD record
ord-854f17e8bcd54347b2d1d54c73847ac3
Source dataset
uspto-grants-1999_09
Patent number
US05955505

Reaction notes

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