3-(4-Hydroxymethyl-2-methyl-phenyl)-acrylic Acid Methyl Ester → 3-(4-Hydroxymethyl-2-methyl-phenyl)-propionic Acid Methyl Ester

HRID 1785208Notes

Reaction equation

HRID 1785208 reaction equation
[CH3:1][O:2][C:3](=[O:15])[CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][OH:13])=[CH:8][C:7]=1[CH3:14].[H][H]>[Ni].O1CCCC1>[CH3:1][O:2][C:3](=[O:15])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][OH:13])=[CH:8][C:7]=1[CH3:14]

Participants

5

Reactant 2

HCID 688380573-(4-Hydroxymethyl-2-methyl-phenyl)-acrylic Acid Methyl EsterHCID 178418361HCID 178418361, compound

Product 1

HCID 574319763-(4-Hydroxymethyl-2-methyl-phenyl)-propionic Acid Methyl Ester

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 3-(4-Hydroxymethyl-2-methyl-phenyl)-acrylic acid methyl ester (4.7 g, 22.8 mmol), Raney nickel (0.668 g) and tetrahydrofuran (618 mL) is shaken under 60 psig. Hydrogen 24 hr. The catalyst is filtered off, and the mixture is concentrated to afford the product as a pale yellow oil, 4.3 g, 91%. The structure is confirmed by 1H NMR spectroscopy.

Workup

  1. filtrationThe catalyst is filtered off
  2. concentrationthe mixture is concentrated

Sources & evidence

ORD record
ord-476e396e96914fcbbcfc72384bc6a297
Source dataset
uspto-grants-2009_03
Patent number
US07504433B2

Reaction notes

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