4-Toluenesulfonyl chloride → (Z)-4-(4-Chlorophenyl)-2-buten-1-ol 4-methylbenzenesulfonate

HRID 464030Notes

Reaction equation

HRID 464030 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8]/[CH:9]=[CH:10]\[CH2:11][OH:12])=[CH:4][CH:3]=1.[OH-:13].[K+].[C:15]1([CH3:25])[CH:20]=[CH:19][C:18]([S:21](Cl)(=[O:23])=[O:22])=[CH:17][CH:16]=1>CCOCC>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8]/[CH:9]=[CH:10]\[CH2:11][OH:12])=[CH:6][CH:7]=1.[CH3:25][C:15]1[CH:20]=[CH:19][C:18]([S:21]([O-:23])(=[O:22])=[O:13])=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 14797Potassium HydroxideHCID 13660260HCID 13660260, compound

Product 1

HCID 131714350(Z)-4-(4-Chlorophenyl)-2-buten-1-ol 4-methylbenzenesulfonate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Dissolve 7.3 g (0.04 mole) of (Z)-4-(4-chlorophenyl)but-2-en-ol in 100 ml of anhydrous ether. Add 3.2 g (0.05 mole) of powdered 86% KOH. Stir and cool the mixture in ice bath while adding a solution of 8.4 g (0.044 mole) of p-toluenesulfonyl chloride in 50 ml of anhydrous ether. Slowly warm the reaction mixture to room temperature and stir at room temperature for 16 hours. Remove the solid by filtration. Wash the filtrate with saturated aqueous sodium bicarbonate, H2O. Dry, evaporate, and recrystallize from cyclohexane to yield the title compound.

Workup

  1. temperaturecool the mixture in ice bath
  2. stirringstir at room temperature for 16 hours
  3. customRemove the solid
  4. filtrationby filtration
  5. washWash the filtrate with saturated aqueous sodium bicarbonate, H2O
  6. customDry
  7. customevaporate
  8. customrecrystallize from cyclohexane

Sources & evidence

ORD record
ord-c561988f1b4741a29d719acbe2eb3f19
Source dataset
uspto-grants-1985_10
Patent number
US04545995

Reaction notes

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