4-Chlorophenol → HCID 14700140, compound

HRID 704522Notes

Reaction equation

HRID 704522 reaction equation
Br[CH2:2][C:3]([C:5]1([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:7][CH2:6]1)=[O:4].C(=O)([O-])[O-].[K+].[K+].[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=1>CC(C)=O>[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][CH2:2][C:3]([C:5]2([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:7][CH2:6]2)=[O:4])=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 46844-ChlorophenolHCID 11430Potassium CarbonateHCID 11436266Ethyl 1-(2-bromoacetyl)cyclopropanecarboxylate

Product 1

HCID 14700140HCID 14700140, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

47.2 g (0.2 mol) of ethyl 1-(bromoacetyl)-cyclopropanecarboxylate are added to a suspension of b 28 g (0.2 mol) of potassium carbonate and 26 g (0.2 mol) of 4-chlorophenol in 300 ml of acetone and the mixture is heated under reflux for 6 hours. Inorganic salts are then filtered off, the filtrate is concentrated under reduced pressure and the residue is distilled in vacuo. 39 g (69% of theory) of ethyl 1-(4-chlorophenoxyacetyl)-cyclopropanecarboxylate are obtained. B.P. 148°-150° C./0.45 mbar.

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 6 hours
  3. filtrationInorganic salts are then filtered off
  4. concentrationthe filtrate is concentrated under reduced pressure
  5. distillationthe residue is distilled in vacuo

Sources & evidence

ORD record
ord-85bc64702a72428596020808bd7cbbcd
Source dataset
uspto-grants-1991_01
Patent number
US04988383

Reaction notes

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