Trimethyl orthoacetate → Methyl 2-nitro-4-(trifluoromethyl)benzoate

HRID 1698597Notes

Reaction equation

HRID 1698597 reaction equation
[N+:1]([C:4]1[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=[O:7])([O-:3])=[O:2].[C:17](OC)(OC)(OC)C>C1(C)C=CC=CC=1>[N+:1]([C:4]1[CH:12]=[C:11]([C:13]([F:14])([F:15])[F:16])[CH:10]=[CH:9][C:5]=1[C:6]([O:8][CH3:17])=[O:7])([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 15050Trimethyl orthoacetateHCID 6420962-Nitro-4-(trifluoromethyl)benzoic acid

Product 1

HCID 11276727Methyl 2-nitro-4-(trifluoromethyl)benzoate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2-nitro-4-trifluoromethylbenzoic acid (23.5 g, 0.10 mol), trimethyl orthoacetate (60.1 g, 0.50 mol) and toluene (60 ml) was heated at 80° C. for 16 h. The reaction mixture was concentrated in vacuo. Toluene was added and concentrated again to remove excess reagent. The residue was purified by column chromatography on silica gel with a 1-10% ethyl acetate/n-hexane gradient mixture to give 24.9 g (0.50 mol 100%) of the title compound as a colorless oil.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionToluene was added
  3. concentrationconcentrated again
  4. customto remove excess reagent
  5. customThe residue was purified by column chromatography on silica gel with a 1-10% ethyl acetate/n-hexane gradient mixture

Sources & evidence

ORD record
ord-11d3c4c5fa194ca39d307913d3ee2a56
Source dataset
uspto-grants-2012_04
Patent number
US08163935B2

Reaction notes

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