Potassium Hydroxide → 3-(3-Chlorophenylthio)-4-oxocyclohexaneacetic acid ethyl ester

HRID 1856521Notes

Reaction equation

HRID 1856521 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([SH:8])[CH:5]=[CH:6][CH:7]=1.[OH-].[K+].[CH2:11]([O:13][C:14](=[O:24])[CH2:15][CH:16]1[CH2:21][CH2:20][C:19](=[O:22])[CH:18](Br)[CH2:17]1)[CH3:12]>C(O)C>[CH2:11]([O:13][C:14](=[O:24])[CH2:15][CH:16]1[CH2:21][CH2:20][C:19](=[O:22])[CH:18]([S:8][C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=2)[CH2:17]1)[CH3:12]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 162573-ChlorothiophenolHCID 130650933-Bromo-4-ketocyclohexaneacetic acid ethyl ester

Product 1

HCID 130651313-(3-Chlorophenylthio)-4-oxocyclohexaneacetic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

In a 3-l. three-necked flask, provided with a condenser, nitrogen inlet, dropping funnel and stirrer were placed 23.8 g. of 3-chlorothiophenol and a solution of 10.8 g. of 85% potassium hydroxide in 300 ml. of ethanol. The solution was brought to reflux, and a solution of 43 g. of 3-bromo-4-oxocyclohexaneacetic acid ethyl ester in 250 ml. of ethanol was added over a period of one hour. After the addition, the solution was stirred at reflux for one hour, cooled to room temperature and filtered to remove the potassium bromide. After removal of the ethanol in vacuo on the steam bath, 150 ml. of water was added to the residue, the product extracted three times with 100 ml. of ether, and the ether extract was dried over anhydrous magnesium sulfate. After removal of the ether from a steam bath at atmospheric pressure, the residue was distilled in vacuo. The yield of 3-(3-chlorophenylthio)-4-oxocyclohexaneacetic acid ethyl ester was 12.2 g.; b.p. 195°-225°/2 mm.

Workup

  1. customthree-necked flask, provided with a condenser, nitrogen inlet
  2. temperatureto reflux
  3. additionAfter the addition
  4. temperatureat reflux for one hour
  5. filtrationfiltered
  6. customto remove the potassium bromide
  7. customAfter removal of the ethanol in vacuo on the steam bath, 150 ml
  8. additionof water was added to the residue
  9. extractionthe product extracted three times with 100 ml
  10. extractionof ether, and the ether extract
  11. dry with materialwas dried over anhydrous magnesium sulfate
  12. customAfter removal of the ether from a steam bath at atmospheric pressure
  13. distillationthe residue was distilled in vacuo

Sources & evidence

ORD record
ord-9e23dc9b8a5a4943b72aae1c6d14f82d
Source dataset
uspto-grants-1980_08
Patent number
US04219657

Reaction notes

Loading…