Potassium Hydroxide → HCID 53942620, compound

HRID 971876Notes

Reaction equation

HRID 971876 reaction equation
[CH3:1][CH2:2][O:3][C:4]([CH:6]1[C:10](=[O:11])[CH2:9][CH2:8][CH2:7]1)=[O:5].Cl[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:16][CH:15]=1.[OH-].[K+]>CN(C)C=O.C(O)(=O)C>[CH2:2]([O:3][C:4]([C:6]1([CH2:13][C:14]2[CH:15]=[CH:16][C:17]([CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:18][CH:19]=2)[CH2:7][CH2:8][CH2:9][C:10]1=[O:11])=[O:5])[CH3:1]

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 69136Ethyl 2-oxocyclopentanecarboxylateHCID 12799528Ethyl [4-(chloromethyl)phenyl]acetate

Product 1

HCID 53942620HCID 53942620, compoundYield 72.4%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
50 °C

Procedure

A mixture of 9.4 g of ethyl 2-cyclopentanonecarboxylate, 10.6 g of ethyl p-chloromethylphenylacetate, 3.58 g of potassium hydroxide and 60 ml of dimethyl formamide was stirred at room temperature for 5 hours, at 50° C. for 1 hour and thereafter at room temperature overnight. The reaction mixture was acidified by addition of acetic acid, dimethyl formamide was removed by distillation, water was added to the residue, and the mixture was extracted with ether. The extract was washed with water, dried over anhydrous sodium sulfate, and the solvent evaporated to give an oily substance, which was subjected to a vacuum distillation affording 12 g of the desired compound, b.p. 180°-190° C. at 0.8 mm Hg.

Workup

  1. customat room temperature
  2. customovernight
  3. customwas removed by distillation, water
  4. additionwas added to the residue
  5. extractionthe mixture was extracted with ether
  6. washThe extract was washed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. customthe solvent evaporated
  9. customto give an oily substance, which
  10. distillationwas subjected to a vacuum distillation

Sources & evidence

ORD record
ord-381acb6715ca46f4bf5cfc5408467c13
Source dataset
uspto-grants-1979_07
Patent number
US04161538

Reaction notes

Loading…