2-[4-(4-Chlorophenyl)phenyl]-5,5-dimethyl-1,3-dioxolan-4-one → Clobuzarit

HRID 1702542Notes

Reaction equation

HRID 1702542 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH:14]3[O:18][C:17](=[O:19])[C:16]([CH3:21])([CH3:20])[O:15]3)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[H][H]>[Pd].C(O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][O:15][C:16]([CH3:21])([CH3:20])[C:17]([OH:19])=[O:18])=[CH:10][CH:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 127737612-[4-(4-Chlorophenyl)phenyl]-5,5-dimethyl-1,3-dioxolan-4-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 71697Clobuzarit

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Palladium on carbon (5% w/w, 0.1 g.) was added to a solution of 2-[4-(4-chlorophenyl)-phenyl]-5,5-dimethyl-1,3-dioxolan-4-one (0.3 g.) in ethanol (50 ml.). The suspension was treated with hydrogen gas at 25° C. and atmospheric pressure for 1.5 hours. The catalyst was removed by filtration and the filtrate evaporated. The residue was dissolved in toluene (10 ml.) and the solution obtained was extracted with 1 M sodium hydroxide solution (10 ml.). The aqueous extracts were acidified with 2 M hydrochloric acid and extracted with toluene (2×10 ml.). By evaporation of the toluene extracts, there may thus be obtained 2-[4-(4-chlorophenyl)benzyloxy]-2-methylpropionic acid, as a waxy solid equivalent to that obtained in Example 12.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe filtrate evaporated
  3. dissolutionThe residue was dissolved in toluene (10 ml.)
  4. customthe solution obtained
  5. extractionwas extracted with 1 M sodium hydroxide solution (10 ml.)
  6. extractionextracted with toluene (2×10 ml.)
  7. customBy evaporation of the toluene

Sources & evidence

ORD record
ord-d610deb9282a403d868c8c761496d589
Source dataset
uspto-grants-1982_09
Patent number
US04348322

Reaction notes

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