Methanol → 2-(3-Methylphenyl)propanoic acid

HRID 851469Notes

Reaction equation

HRID 851469 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-3cacadba644847148b1f7f076a9e86a5
Source dataset
uspto-grants-1983_05
Patent number
US04385004

Reaction notes

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