Triethylamine → 2-Benzyl-3-hydroxypropanoic acid

HRID 1066454Notes

Reaction equation

HRID 1066454 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.C(N(CC)CC)C.[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

6

Reactant 3

HCID 8471TriethylamineHCID 538146242-benzylidene-3-hydroxypropionic AcidHCID 178418361HCID 178418361, compound

Product 1

HCID 5623452-Benzyl-3-hydroxypropanoic acidYield 89.3%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

2-Benzylidene-3-hydroxypropionic acid (79.96 g, 449 mmols) obtained in Example 7 was dissolved in 500 ml of methanol, and 100 ml (717 mmols) of triethylamine and 5.00 g (water content 52.7%) of 5% palladium-carbon were added thereto to conduct catalytic reduction in a hydrogen atmosphere for 7 hours. After the completion of the reaction, the palladium-carbon was removed from the reaction solution through filtration with Celite. The HPLC analysis of the resulting filtrate revealed that it contained 72.3 g (401 mmols) of the above title compound (reaction yield 89.3%).

Workup

  1. customfor 7 hours
  2. customAfter the completion of the reaction
  3. customthe palladium-carbon was removed from the reaction solution through filtration with Celite

Sources & evidence

ORD record
ord-7cffbd0c9eab48028ee2a20cf1a49ee4
Source dataset
uspto-grants-2001_06
Patent number
US06242635B1

Reaction notes

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