4-Toluenesulfonyl chloride → HCID 86745160, compound

HRID 345451Notes

Reaction equation

HRID 345451 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[Cl:12][C:13]1[CH:18]=[CH:17][C:16](/[CH:19]=[C:20](\[CH2:26][OH:27])/[CH2:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[CH:15][CH:14]=1.C(N(CC)CC)C>C(Cl)Cl>[Cl:12][C:13]1[CH:14]=[CH:15][C:16](/[CH:19]=[C:20](\[CH2:26][O:27][S:8]([C:5]2[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=2)(=[O:10])=[O:9])/[CH2:21][C:22]([CH3:23])([CH3:24])[CH3:25])=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 67937970HCID 67937970, compound

Product 1

HCID 86745160HCID 86745160, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

42 g of 4-methylbenzenesulfonyl chloride are added to a solution of 45.8 g of Z-1-(4-chlorophenyl)-2-hydroxymethyl-4,4-dimethylpent-1-ene in 200 ml of methylene chloride and 59 g of triethylamine at room temperature. After 24 hours, the reaction mixture is washed with aqueous sodium bicarbonate solution and water, dried over sodium sulfate and evaporated down under reduced pressure. The residue gives 73.1 g (98%) of Z-1-(4-chlorophenyl)-2-(4-methylphenylsulfonyloxymethyl)-4,4-dimethylpent-1-ene.

Workup

  1. washthe reaction mixture is washed with aqueous sodium bicarbonate solution and water
  2. dry with materialdried over sodium sulfate
  3. customevaporated down under reduced pressure

Sources & evidence

ORD record
ord-cac687f34fe24948bf593b59b461e618
Source dataset
uspto-grants-1991_10
Patent number
US05057531

Reaction notes

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