Acetyl chloride → Methyl 3-nitro-5-(trifluoromethyl)benzoate

HRID 534837Notes

Reaction equation

HRID 534837 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:12]=1)[C:7]([OH:9])=[O:8])([O-:3])=[O:2].[C:17](Cl)(=O)C>CO>[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[C:11]([C:13]([F:14])([F:15])[F:16])[CH:12]=1)[C:7]([O:9][CH3:17])=[O:8])([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 6166023-Nitro-5-(trifluoromethyl)benzoic acid

Product 1

HCID 18942157Methyl 3-nitro-5-(trifluoromethyl)benzoateYield 93.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To an ice cooled stirred solution of 3-nitro-5-(trifluoromethyl)benzoic acid (25.00 g, 106.3 mmol) in methanol (500 mL) was added acetyl chloride (22.00 g, 280.2 mmol) dropwise over 20 min. After the addition was complete, the reaction mixture was stirred for 20 min at 0° C., then heated at reflux for 6 h and then cooled to room temperature. The reaction mixture was concentrated under reduced pressure and the residue was dissolved in ethyl acetate, washed with saturated aqueous sodium bicarbonate, filtered through a silica gel and concentrated under reduced pressure to provide methyl 3-nitro-5-(trifluoromethyl)benzoate (24.65 g, 93%) as a pale yellow oil.

Workup

  1. additionAfter the addition
  2. temperatureheated
  3. temperatureat reflux for 6 h
  4. temperaturecooled to room temperature
  5. concentrationThe reaction mixture was concentrated under reduced pressure
  6. dissolutionthe residue was dissolved in ethyl acetate
  7. washwashed with saturated aqueous sodium bicarbonate
  8. filtrationfiltered through a silica gel
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c3848884e18b4e9e8985bb5c57ce8933
Source dataset
uspto-grants-2014_10
Patent number
US08853215B2

Reaction notes

Loading…