Hydrochloric Acid → 4-Nitro-3-trifluoromethyl-phenoxyethyl acetate

HRID 383534

Reaction equation

HRID 383534 reaction equation
Br[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[N+:8]([C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][C:12]=1[C:18]([F:21])([F:20])[F:19])([O-:10])=[O:9].C(=O)([O-])[O-].[K+].[K+].Cl>CC(C)=O>[C:3]([O:5][CH2:6][CH2:7][O:17][C:14]1[CH:15]=[CH:16][C:11]([N+:8]([O-:10])=[O:9])=[C:12]([C:18]([F:19])([F:20])[F:21])[CH:13]=1)(=[O:4])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 69314-Nitro-3-trifluoromethylphenolHCID 7748Ethyl bromoacetateHCID 11430Potassium Carbonate

Product 1

HCID 675200144-Nitro-3-trifluoromethyl-phenoxyethyl acetateYield 114.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Ethyl bromoacetate (1.2 g, 10.9 mmol) was added in the suspension of 4-nitro-3-trifluoromethyl phenol (2.0 g, 9.66 mmol) and potassium carbonate (2.0 g, 14.5 mmol) in acetone, and the mixture was attired at room temperature for 6 hours. After the reaction mixture had been poured in ice water and acidified with 2N hydrochloric acid, the mixture was extracted with ethyl acetate. The organic layer was washed with 5% sodium hydrogencarbonate aqueous solution and then with water, and dried with anhydrous sodium sulfate. The solvent was removed by distillation under reduced pressure, and 4-nitro-3-trifluoromethyl-phenoxyethyl acetate (3.24 g (theoretical amount: 2.83 g), 100%) was obtained as a yellow solid and was used in the next reaction without purification.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with 5% sodium hydrogencarbonate aqueous solution
  3. dry with materialwith water, and dried with anhydrous sodium sulfate
  4. customThe solvent was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-ddfbbc03f67d4b479bc0597f136195a4
Source dataset
uspto-grants-2013_02
Patent number
US08367666B2

Linked notes

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