Water → HCID 13556590, compound

HRID 638602Notes

Reaction equation

HRID 638602 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].O.Cl[CH2:17][C:18](=[O:25])[C:19]([CH3:24])([CH3:23])[CH2:20][CH2:21][Cl:22]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:17][C:18](=[O:25])[C:19]([CH3:24])([CH3:23])[CH2:20][CH2:21][Cl:22])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 7815p-ChlorothiophenolHCID 11430Potassium CarbonateHCID 132542791,5-Dichloro-3,3-dimethylpentan-2-one

Product 1

HCID 13556590HCID 13556590, compoundYield 94.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
100 °C

Procedure

86.7 g (0.6 mole) of 4-chlorothiophenol and 82.8 g (0.6 mole) of potassium carbonate in 500 ml of toluene are heated under reflux for 2 hours, using a water separator. 91.5 g (0.5 mole) of 1,5-dichloro-3,3-dimethyl-2-pentanone in 200 ml of toluene are then added at 100° C. The reaction mixture is stirred at 100° C. for 5 hours and is then allowed to cool, and is stirred with 500 ml of water. The organic phase is separated off, washed with dilute sodium hydroxide solution and with water, dried over sodium sulphate and concentrated. 137.4 g (94.4% of theory) of 1-(4-chlorophenylthio)-5-chloro-3,3-dimethyl-2-pentanone of refractive index nD20 1.5628 are obtained. ##STR95##

Workup

  1. temperatureunder reflux for 2 hours
  2. temperatureto cool
  3. customThe organic phase is separated off
  4. washwashed with dilute sodium hydroxide solution and with water
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-4f8b6d35740643498a16f0caeae69abc
Source dataset
uspto-grants-1985_12
Patent number
US04562198

Reaction notes

Loading…