2-[4-(4-Chlorophenyl)phenyl]-5-ethyl-5-phenyl-1,3-dioxolan-4-one → 2-[4-(4-Chlorophenyl)benzyloxy]-2-phenylbutyric acid

HRID 1702540Notes

Reaction equation

HRID 1702540 reaction equation
[H][H].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13]([CH:16]3[O:20][C:19](=[O:21])[C:18]([CH2:28][CH3:29])([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[O:17]3)=[CH:12][CH:11]=2)=[CH:6][CH:5]=1>[Pd].C(O)C.C1(C)C=CC=CC=1>[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][O:17][C:18]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)([CH2:28][CH3:29])[C:19]([OH:21])=[O:20])=[CH:12][CH:11]=2)=[CH:6][CH:5]=1

Participants

6

Reactant 2

HCID 127737622-[4-(4-Chlorophenyl)phenyl]-5-ethyl-5-phenyl-1,3-dioxolan-4-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 103397752-[4-(4-Chlorophenyl)benzyloxy]-2-phenylbutyric acid

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

Hydrogen gas was allowed to react with a stirred suspension of 2-[4-(4-chlorophenyl)phenyl]-5-ethyl-5-phenyl-1,3-dioxolan-4-one (3.8 g.) and 5% w/w palladium on carbon (0.2 g.) in ethanol (160 ml.) at 55° to 60° C. and atmospheric pressure for four hours. The mixture was diluted with toluene (50 ml.). The solid material was separated by filtration and the filtrate was evaporated. The resultant solid may be purified by high pressure liquid chromatography on "Spherisorb"* 5μ ODS solid phase using an eluant containing acetonitrile (62% v/v), water (37.9% v/v) and phosphoric acid (0.1% v/v) using ultraviolet absorbance at 262 μm for detection to give 2-[4-(4-chlorophenyl)benzyloxy]-2-phenylbutyric acid identical to that obtained in previous examples.

Workup

  1. customThe solid material was separated by filtration
  2. customthe filtrate was evaporated
  3. customThe resultant solid may be purified by high pressure liquid chromatography on "Spherisorb"* 5μ ODS solid phase
  4. additioncontaining acetonitrile (62% v/v), water (37.9% v/v) and phosphoric acid (0.1% v/v)

Sources & evidence

ORD record
ord-d75311eeeefc4893bef64b87166c0a1a
Source dataset
uspto-grants-1982_09
Patent number
US04348322

Reaction notes

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