Methanol → 2-(3-Methylphenyl)propanoic acid

HRID 358287Notes

Reaction equation

HRID 358287 reaction equation
S(O[C:6]1[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][C:7]=1[CH:8]([CH3:12])[C:9]([OH:11])=[O:10])(C)(=O)=O.CO.[H][H]>[Pd].C(N(CC)CC)C>[CH3:17][C:14]1[CH:13]=[C:7]([CH:6]=[CH:16][CH:15]=1)[CH:8]([CH3:12])[C:9]([OH:11])=[O:10]

Participants

6

Reactant 3

HCID 887MethanolHCID 204498382-Mesyloxy-5-methyl-hydratropic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 52497092-(3-Methylphenyl)propanoic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8471TriethylamineSolvent

Procedure

To a solution of 1.29 g. of 2-mesyloxy-5-methyl-hydratropic acid in 25 ml. of methanol 1.4 ml. of triethylamine and 0.2 g. of a 5% palladium-on-charcoal catalyst are added. The mixture is hydrogenated at 25° C., under atmospheric pressure until the calculated amount of hydrogen is used up. The catalyst is filtered off and the solution is evaporated. The evaporation residue is taken up in water, acidified with a 20% aqueous hydrochloric acid solution and shaken with ether. Ether is distilled off to give 3-methyl-hydratropic acid as an oily residue. The corresponding cyclohexylamine salt melts at 168° C. to 169° C.

Workup

  1. filtrationThe catalyst is filtered off
  2. customthe solution is evaporated
  3. distillationEther is distilled off

Sources & evidence

ORD record
ord-b7c2b2ad7d2840c787b4702d5295dfaa
Source dataset
uspto-grants-1984_08
Patent number
US04465855

Reaction notes

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