2-Hydroxy-4-methyl-hydratropic acid phenylurethane → 2-(4-Tolyl)propanoic acid

HRID 358286

Reaction equation

HRID 358286 reaction equation
C1(NC(OCC)=O)C=CC=CC=1.O[C:14]1[CH:24]=[C:23]([CH3:25])[CH:22]=[CH:21][C:15]=1[CH:16]([CH3:20])[C:17]([OH:19])=[O:18].[H][H]>C(O)(=O)C.[Pd]>[CH3:25][C:23]1[CH:22]=[CH:21][C:15]([CH:16]([CH3:20])[C:17]([OH:19])=[O:18])=[CH:14][CH:24]=1

Participants

5

Reactant 2

HCID 705129172-Hydroxy-4-methyl-hydratropic acid phenylurethaneHCID 178418361HCID 178418361, compound

Product 1

HCID 1508662-(4-Tolyl)propanoic acidYield 67%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

3 g. of 2-hydroxy-4-methyl-hydratropic acid phenylurethane are dissolved in acetic acid. To the solution 0.4 g. of a 5% palladium-on-charcoal catalystand the mixture is hydrogenated at 25° C. until the calculated amount of hydrogen is used up. The catalyst is filtered off and the filtrate is evaporated. The residue is admixed with a 10% aqueous hydrochloric acid solution and the separated oil is extracted with chloroform. The chloroform solution is dried over sodium sulphate and evaporated. 1.1 g. (67%) of 4-methyl-hydratropic acid are obtained.

Workup

  1. filtrationThe catalyst is filtered off
  2. customthe filtrate is evaporated
  3. extractionthe separated oil is extracted with chloroform
  4. dry with materialThe chloroform solution is dried over sodium sulphate
  5. customevaporated

Sources & evidence

ORD record
ord-63815bf459344ee2a79fc079d2e70945
Source dataset
uspto-grants-1984_08
Patent number
US04465855

Linked notes

Loading…