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

HRID 2058551Notes

Reaction equation

HRID 2058551 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 catalyst are added, and 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-2263ebcd68ac489b8bb44fe2110f7e35
Source dataset
uspto-grants-1982_03
Patent number
US04317920

Reaction notes

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