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

HRID 65236Notes

Reaction equation

HRID 65236 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:12])/[CH:9]=[CH:10]\[CH3:11])=[CH:4][CH:3]=1.[OH-].[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:7]=[CH:6][C:5]([CH2:8]/[CH:9]=[CH:10]\[CH2:11][OH:22])=[CH:4][CH:3]=1.[CH3:25][C:15]1[CH:20]=[CH:19][C:18]([S:21]([O-:12])(=[O:23])=[O:22])=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 14797Potassium HydroxideHCID 67901371(Z)-1-(4-chlorophenyl)-2-buten-1-ol

Product 1

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

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Dissolve 6.7 g (0.036 mole) of (Z)-1-(4-chlorophenyl)-2-buten-1-ol in 100 ml of anhydrous ether, add 3.2 g of powdered KOH. Stir the mixture and with cooling add a solution of 7.0 g p-toluenesulfonylchloride in 30 ml of anhydrous ether. Continue to stir with cooling for 30 minutes, then allow to warm to room temperature overnight. Filter, wash the filtrate three times with saturated aqueous sodium bicarbonate, then with water and dry over sodium sulfate. Evaporate off solvents and triturate residue with petroleum ether, cyclohexane. Recrystallize residue from cyclohexane to yield the title compound.

Workup

  1. temperaturewith cooling
  2. stirringto stir
  3. temperaturewith cooling for 30 minutes
  4. filtrationFilter
  5. washwash the filtrate three times with saturated aqueous sodium bicarbonate
  6. dry with materialwith water and dry over sodium sulfate
  7. customEvaporate off solvents
  8. customtriturate residue with petroleum ether, cyclohexane

Sources & evidence

ORD record
ord-92e7a273e5d349b09985d91a70505cc0
Source dataset
uspto-grants-1986_09
Patent number
US04613609

Reaction notes

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