2-Chlorophenol → HCID 14348248, compound

HRID 2164992Notes

Reaction equation

HRID 2164992 reaction equation
BrBr.Cl[CH2:4][CH2:5][CH2:6][C:7](=[O:9])[CH3:8].C(=O)([O-])[O-].[K+].[K+].[Cl:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[OH:23]>C(Cl)Cl.CN(C)C=O.O>[C:7]([C:6]1([O:23][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[Cl:16])[CH2:4][CH2:5]1)(=[O:9])[CH3:8]

Participants

8

Reactant 4

HCID 72452-ChlorophenolHCID 11430Potassium CarbonateHCID 24408BromineHCID 799932-Pentanone, 5-chloro-

Product 1

HCID 14348248HCID 14348248, compoundYield 53%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 134 g (0.84 mol) of bromine in 130 ml of methylene chloride is added dropwise at 10° C. with stirring to a mixture of 100 g (0.83 mol) of 5-chloropentan-2-one and 400 ml of methylene chloride. After completion of the addition, the reaction mixture is stirred for a further 15 minutes and then poured into 500 ml of water. The organic phase is separated off, washed successively with 5% strength aqueous sodium carbonate solution and with water, then dried over sodium sulphate and concentrated by stripping off the solvent under reduced pressure. The residue is taken up in 200 ml of dimethylformamide, and the resulting solution is added dropwise at 60° C. to a mixture of 230 g of potassium carbonate, 106 g (0.83 mol) of 2-chlorophenol and 400 ml of dimethylformamide. The reaction mixture is initially stirred for 4 hours at 60° C. and then for 4 hours at 90° C. The mixture is then filtered from the solid residue with suction, the solvent is stripped off under reduced pressure and the remaining residue is taken up in a mixture of ethyl acetate and toluene. The organic phase is washed with water, dried over sodium sulphate and concentrated by stripping off the solvent under reduced pressure. The remaining residue is subjected to a vacuum distillation. In this manner, 92.5 g (53% of theory) of 1-acetyl-1-(2-chlorophenoxy)-cyclopropane are obtained in the form of a liquid of boiling point 81° C./0.2 mbar.

Workup

  1. additionAfter completion of the addition
  2. customThe organic phase is separated off
  3. washwashed successively with 5% strength aqueous sodium carbonate solution and with water
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated
  6. stirringThe reaction mixture is initially stirred for 4 hours at 60° C.
  7. waitfor 4 hours at 90° C
  8. filtrationThe mixture is then filtered from the solid residue with suction
  9. additionthe remaining residue is taken up in a mixture of ethyl acetate and toluene
  10. washThe organic phase is washed with water
  11. dry with materialdried over sodium sulphate
  12. concentrationconcentrated
  13. distillationThe remaining residue is subjected to a vacuum distillation

Sources & evidence

ORD record
ord-9bd96def1d884543bfcec23bc77541fb
Source dataset
uspto-grants-1990_07
Patent number
US04938791

Reaction notes

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