Methyl 2-benzylidene-3-hydroxypropionate → Methyl 2-benzyl-3-hydroxypropanoate

HRID 1066457Notes

Reaction equation

HRID 1066457 reaction equation
[CH:1](=[C:8]([CH2:13][OH:14])[C:9]([O:11][CH3:12])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H][H]>CO.[C].[Pd]>[OH:14][CH2:13][CH:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:9]([O:11][CH3:12])=[O:10]

Participants

5

Reactant 2

HCID 54265908Methyl 2-benzylidene-3-hydroxypropionateHCID 178418361HCID 178418361, compound

Product 1

HCID 10702975Methyl 2-benzyl-3-hydroxypropanoateYield 99.2%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

Methyl 2-benzylidene-3-hydroxypropionate (847.2 mg, 4.408 mmols) was dissolved in 8 ml of methanol, and 21.7 mg (water content 2.7%) of 5% palladium-carbon were added thereto to conduct catalytic reduction in a hydrogen atmosphere for 140 minutes. After the completion of the reaction, the reaction solution was filtered with Celite to remove the palladium-carbon. The resulting solution was concentrated under reduced pressure to obtain 849.2 mg of a crude product of the above title compound.

Workup

  1. customfor 140 minutes
  2. customAfter the completion of the reaction
  3. filtrationthe reaction solution was filtered with Celite
  4. customto remove the palladium-carbon
  5. concentrationThe resulting solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-ac2cd444adcd45c6bc9499aa450d648a
Source dataset
uspto-grants-2001_06
Patent number
US06242635B1

Reaction notes

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