(E)-3-(3-Hydroxymethyl-phenyl)-acrylic acid methyl ester → Methyl 3-[3-(hydroxymethyl)phenyl]propanoate

HRID 15006Notes

Reaction equation

HRID 15006 reaction equation
[CH3:1][O:2][C:3](=[O:14])/[CH:4]=[CH:5]/[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH2:12][OH:13])[CH:7]=1>C(O)C>[CH3:1][O:2][C:3](=[O:14])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH2:12][OH:13])[CH:7]=1

Participants

3

Reactant 1

HCID 59794688(E)-3-(3-Hydroxymethyl-phenyl)-acrylic acid methyl ester

Product 1

HCID 59794668Methyl 3-[3-(hydroxymethyl)phenyl]propanoateYield 83.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(Ph3P)3RhCl (11.5 mg, 0.012 mmol) was added to a solution of 17 (25 mg, 0.13 mmol) in 0.400 mL ethanol. The reaction was stirred under 1 atm H2 balloon for 20 h and then was filtered through Celite. Evaporation to dryness and purification by flash chromatography on silica gel (30% ethyl acetate/hexanes) gave compound 18 (21 mg, 82%).

Workup

  1. filtrationwas filtered through Celite
  2. customEvaporation
  3. customto dryness and purification by flash chromatography on silica gel (30% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-e6ff693431444151971f276948e1e778
Source dataset
uspto-grants-2010_06
Patent number
US07732443B2

Reaction notes

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