2-Propenoic acid, 3-(4-formylphenyl)- → 3-[4-(Hydroxymethyl)phenyl]propanoic acid

HRID 2261435Notes

Reaction equation

HRID 2261435 reaction equation
[CH:1]([C:3]1[CH:13]=[CH:12][C:6]([CH:7]=[CH:8][C:9]([OH:11])=[O:10])=[CH:5][CH:4]=1)=[O:2]>C(O)C.CCN(C(C)C)C(C)C.[Pd]>[OH:2][CH2:1][C:3]1[CH:13]=[CH:12][C:6]([CH2:7][CH2:8][C:9]([OH:11])=[O:10])=[CH:5][CH:4]=1

Participants

5

Reactant 1

HCID 980772-Propenoic acid, 3-(4-formylphenyl)-

Product 1

HCID 203221243-[4-(Hydroxymethyl)phenyl]propanoic acidYield 75.6%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 81531DiisopropylethylamineSolvent

Procedure

A mixture of 4-formyl cinnamic acid (2.82 g, 16.0 mmol) and Pd/C (350 mg, 10% Pd) in ethanol (120 mL) and DIPEA (3 mL) is stirred at rt for 2 h under 1.0 bar H2. The reaction mixture is filtered and the filtrate is evaporated to give 3-(4-hydroxymethyl-phenyl)-propionic acid (2.18 g) as a colourless oil; LC-MS: tR=0.62 min.

Workup

  1. filtrationThe reaction mixture is filtered
  2. customthe filtrate is evaporated

Sources & evidence

ORD record
ord-265c7446df644cdf9484ca1a7e86c8b1
Source dataset
uspto-grants-2010_12
Patent number
US07846964B2

Reaction notes

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