4-Methylbenzenethiol → HCID 53657949, compound

HRID 1856525Notes

Reaction equation

HRID 1856525 reaction equation
[C:1]1([CH3:8])[CH:6]=[CH:5][C:4]([SH:7])=[CH:3][CH:2]=1.[OH-].[K+].[CH2:11]([O:13][C:14]([CH:16]1[CH2:21][CH2:20][C:19](=[O:22])[CH:18](Br)[CH2:17]1)=[O:15])[CH3:12]>C(O)C>[CH2:11]([O:13][C:14]([CH:16]1[CH2:21][CH2:20][C:19](=[O:22])[CH:18]([S:7][C:4]2[CH:5]=[CH:6][C:1]([CH3:8])=[CH:2][CH:3]=2)[CH2:17]1)=[O:15])[CH3:12]

Participants

5

Reactant 3

HCID 78114-MethylbenzenethiolHCID 14797Potassium HydroxideHCID 12917737Ethyl 3-bromo-4-oxocyclohexane-1-carboxylate

Product 1

HCID 53657949HCID 53657949, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

In a 2 l. three-necked flask provided with a condenser, nitrogen inlet, dropping funnel and stirrer were placed 73.5 g. of p-toluenethiol and a solution of 33 g. of 85% potassium hydroxide in 500 ml. of ethanol. The solution was brought to reflux, and a solution of 146.4 g. of 3-bromo-4-ketocyclohexanecarboxylic acid ethyl ester in 500 ml. of ethanol was added over a period of one hour. After the addition, the solution was stirred at reflux for one hour. After removal of the ethanol in vacuo on the steam bath, 300 ml. of water was added, and the product was extracted three times with 200 ml. of ether. The ether solution was dried over anhydrous magnesium sulfate, and then the solvent was removed on the steam bath. The residue was crystallized from heptane; yield 66 g. of 3-(4-methylphenylthio)-4-ketocyclohexanecarboxylic acid ethyl ester, m.p. 87°-89°.

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. customAfter removal of the ethanol in vacuo on the steam bath, 300 ml
  6. additionof water was added
  7. extractionthe product was extracted three times with 200 ml
  8. dry with materialThe ether solution was dried over anhydrous magnesium sulfate
  9. customthe solvent was removed on the steam bath
  10. customThe residue was crystallized from heptane

Sources & evidence

ORD record
ord-fc2756f5d16443eb9c19f32c23d3c858
Source dataset
uspto-grants-1980_08
Patent number
US04219657

Reaction notes

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