Acetic Anhydride → 2-Ethoxymethylene-1-(2-nitro-4-trifluoromethylphenyl)butan-1,3-dione

HRID 342956Notes

Reaction equation

HRID 342956 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[CH:6][C:5]=1[C:14](=[O:19])[CH2:15][C:16](=[O:18])[CH3:17])([O-:3])=[O:2].[CH:20](OCC)(OCC)[O:21][CH2:22][CH3:23].C(OC(=O)C)(=O)C>>[CH2:22]([O:21][CH:20]=[C:15]([C:16](=[O:18])[CH3:17])[C:14]([C:5]1[CH:6]=[CH:7][C:8]([C:10]([F:11])([F:12])[F:13])=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2])=[O:19])[CH3:23]

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 31214Ethyl orthoformateHCID 540146221-(2-Nitro-4-trifluoromethylphenyl)-butan-1,3-dione

Product 1

HCID 537517422-Ethoxymethylene-1-(2-nitro-4-trifluoromethylphenyl)butan-1,3-dione

Procedure

A mixture of 1-(2-nitro-4-trifluoromethylphenyl)-butan-1,3-dione (-11.0 g), triethyl orthoformate (11.3 g) and acetic anhydride (12.3 g) was stirred and heated at reflux for 3 hours. After cooling, the mixture was evaporated to dryness. Toluene (50 ml) was added and the mixture was evaporated to dryness to give 2-ethoxymethylene-1-(2-nitro-4-trifluoromethylphenyl)-butan-1,3-dione as a crude brown oil which was not further purified.

Workup

  1. temperatureheated
  2. temperatureat reflux for 3 hours
  3. temperatureAfter cooling
  4. customthe mixture was evaporated to dryness
  5. additionToluene (50 ml) was added
  6. customthe mixture was evaporated to dryness

Sources & evidence

ORD record
ord-661bdaa1897f4e9a8ec38002ff25ab30
Source dataset
uspto-grants-1999_01
Patent number
US05859283

Reaction notes

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