Methane → 3-(3,4-dimethylphenyl)propanoic Acid

HRID 1929614Notes

Reaction equation

HRID 1929614 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]([OH:13])=[O:12])[CH:5]=[CH:6][C:7]=1[CH3:8].C>[Pd].CO>[CH3:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][C:11]([OH:13])=[O:12])[CH:5]=[CH:6][C:7]=1[CH3:8]

Participants

5

Reactant 2

HCID 297MethaneHCID 534016643,4-Dimethylcinnamic acid

Product 1

HCID 38702183-(3,4-dimethylphenyl)propanoic Acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 3-(3,4-dimethyl-phenyl)-acrylic acid (19.269 g; 109.355 mmol) and 10% palladium over activated charcoal (1.920 g) was placed under nitrogen before MeOH (300 ml) was carefully added. The resulting suspension was placed under vacuum, then under hydrogen (1 atm), and the reaction mixture was vigorously stirred at rt for 4 h. The reaction mixture was filtered over a pad of celite, and concentrated under reduced pressure to give the expected product 3-(3,4-dimethyl-phenyl)-propionic acid as a grey solid which was further dried under HV (19.070 g; 98%). LC-MS: tR=0.85 min; [M+H]+: no ionisation.

Workup

  1. additionwas carefully added
  2. filtrationThe reaction mixture was filtered over a pad of celite
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9bd7e4d5ab694ba59375853062330669
Source dataset
uspto-grants-2012_05
Patent number
US08188082B2

Reaction notes

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