Phenol → Ethyl 2-(2-nitro-3-phenoxyphenyl)acetate

HRID 2418322Notes

Reaction equation

HRID 2418322 reaction equation
[N+:1]([C:4]1[C:9](Cl)=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])([O-:3])=[O:2].[C:17]1([OH:23])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(=O)([O-])[O-].[K+].[K+]>O>[N+:1]([C:4]1[C:9]([O:23][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 996PhenolHCID 11430Potassium CarbonateHCID 20446267Ethyl 2-(3-chloro-2-nitrophenyl)acetate

Product 1

HCID 20446288Ethyl 2-(2-nitro-3-phenoxyphenyl)acetateYield 28%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of ethyl 2-(2-nitro-3-chlorophenyl)acetate (15 g.), phenol (6.4 g.), anhydrous potassium carbonate (13 g.) and cupric oxide (4.5 g.) was stirred for 4 hours at 120° C. To the reaction mixture was added water and the mixture was extracted with diethyl ether. The extract was washed with a diluted aqueous solution of potassium carbonate and water, dried over magnesium sulfate and then evaporated under reduced pressure. The oily residue was distilled under reduced pressure to give ethyl 2-(2-nitro-3-phenoxypheny)acetate (5.2 g.) bp 160°-183° C./0.4 mmHg.

Workup

  1. extractionthe mixture was extracted with diethyl ether
  2. washThe extract was washed with a diluted aqueous solution of potassium carbonate and water
  3. dry with materialdried over magnesium sulfate
  4. customevaporated under reduced pressure
  5. distillationThe oily residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-2a1690f0d4284562943c7332872e0359
Source dataset
uspto-grants-1984_09
Patent number
US04472433

Reaction notes

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