Toluene → 80854-57-5

HRID 2265114Notes

Reaction equation

HRID 2265114 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][CH:5]=1)=O.[C:13](C=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:15][CH2:16][CH3:17])=[O:14].[C:38]1(C)C=CC=CC=1>>[N+:10]([C:7]1[CH:8]=[CH:9][C:4](/[C:2](/[CH3:38])=[CH:1]/[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:5][CH:6]=1)([O-:12])=[O:11]

Participants

4

Reactant 3

HCID 1140TolueneHCID 7487p-NitroacetophenoneHCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester

Product 1

HCID 614540480854-57-5Yield 29%

Procedure

A toluene (90 ml) solution of 4-nitroacetophenone (2.0 g) and (carbethoxymethylidene)triphenylphosphorane (6.33 g) was stirred while refluxing under heating for 10 hours. After the solution was allowed to cool, the solvent was distilled off. The obtained residue was purified by column chromatography (6.25% ethyl acetate/n-hexane) to obtain Compound 19a (829 mg, 29%) as a white solid.

Workup

  1. temperaturewhile refluxing
  2. temperatureunder heating for 10 hours
  3. temperatureto cool
  4. distillationthe solvent was distilled off
  5. customThe obtained residue was purified by column chromatography (6.25% ethyl acetate/n-hexane)

Sources & evidence

ORD record
ord-d698436e2133487c8add22e095a73a7e
Source dataset
uspto-grants-2010_12
Patent number
US07855300B2

Reaction notes

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