Ammonia → 2-Benzyl-3-hydroxypropanoic acid

HRID 1066455Notes

Reaction equation

HRID 1066455 reaction equation
[CH:1](=[C:8]([CH2:12][OH:13])[C:9]([OH:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N.O.[H][H]>CO.[C].[Pd]>[OH:13][CH2:12][CH:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:9]([OH:11])=[O:10]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 962WaterHCID 538146242-benzylidene-3-hydroxypropionic AcidHCID 178418361HCID 178418361, compound

Product 1

HCID 5623452-Benzyl-3-hydroxypropanoic acidYield 93%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

2-Benzylidene-3-hydroxypropionic acid (490.4 mg, 2.752 mmols) was dissolved in 7 ml of methanol, and 0.5 ml of 28% aqueous ammonia and 2 ml of water were added thereto. Then, 38 mg (water content 52.7%) of 5% palladium-carbon were added thereto, and catalytic reduction was conducted in a hydrogen atmosphere for 160 minutes. After the completion of the reaction, the reaction solution was filtered with Celite to remove the palladium-carbon. The resulting filtrate was subjected to the HPLC analysis. As a result, the filtrate contained 461 mg (2.558 mmols) of the above title compound (yield 93.0%).

Workup

  1. customAfter the completion of the reaction
  2. filtrationthe reaction solution was filtered with Celite
  3. customto remove the palladium-carbon

Sources & evidence

ORD record
ord-ca7a7111294344a4b6ab72e8d666f432
Source dataset
uspto-grants-2001_06
Patent number
US06242635B1

Reaction notes

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