Methanol → 2-Phenylpropionic acid

HRID 851465Notes

Reaction equation

HRID 851465 reaction equation
CS(O[C:6]1[CH:16]=[CH:15][CH:14]=[CH:13][C:7]=1[CH:8]([CH3:12])[C:9]([OH:11])=[O:10])(=O)=O.CO.[H][H]>[Pd].C(N(CC)CC)C>[C:9]([OH:11])(=[O:10])[CH:8]([C:7]1[CH:6]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH3:12]

Participants

6

Reactant 3

HCID 887MethanolHCID 13689664HCID 13689664, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 102962-Phenylpropionic acidYield 90%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8471TriethylamineSolvent

Procedure

To a solution of 24.5 g. of 2-methane-sulphonyloxyhydratropic acid in 200 ml. of methanol 28 ml. of triethylamine and 2 g. of a 5% palladium-on-charcoal catalyst are added. The mixture is hydrogenated at 25° C., under atmospheric pressure until a calculated amount of hydrogen is used up. The catalyst is filtered off and the filtrate is evaporated. The residue is taken up in water and acidified with a 20% aqueous hydrochloric acid solution. The separated hydratropic acid is extracted with chloroform. The chloroform solution is dried over sodium sulphate, evaporated and the residue is distilled off. 13.5 g. (90%) of hydratropic acid are obtained, boiling at 145° C. (13 mmHg.); nD25 =1.5219.

Workup

  1. filtrationThe catalyst is filtered off
  2. customthe filtrate is evaporated
  3. extractionThe separated hydratropic acid is extracted with chloroform
  4. dry with materialThe chloroform solution is dried over sodium sulphate
  5. customevaporated
  6. distillationthe residue is distilled off

Sources & evidence

ORD record
ord-b45fa7d7f06f46da90240cc0899c670d
Source dataset
uspto-grants-1983_05
Patent number
US04385004

Reaction notes

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