4-Toluenesulfonyl chloride → HCID 53721640, compound

HRID 596643Notes

Reaction equation

HRID 596643 reaction equation
[CH3:1][CH:2]([CH2:6][CH2:7][CH:8]=[C:9]([CH3:14])[CH2:10][CH:11]([CH3:13])[CH3:12])[CH2:3][CH2:4][OH:5].[C:15]1([CH3:25])[CH:20]=[CH:19][C:18]([S:21](Cl)(=[O:23])=[O:22])=[CH:17][CH:16]=1>N1C=CC=CC=1>[S:21]([O:5][CH2:4][CH2:3][CH:2]([CH3:1])[CH2:6][CH2:7][CH:8]=[C:9]([CH3:14])[CH2:10][CH:11]([CH3:13])[CH3:12])([C:18]1[CH:19]=[CH:20][C:15]([CH3:25])=[CH:16][CH:17]=1)(=[O:23])=[O:22]

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 53809870HCID 53809870, compound

Product 1

HCID 53721640HCID 53721640, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

79.5 g. of 3,7,9-trimethyl-6-decen-1-ol and 75 ml. of pyridine are treated portionwise with 76 g. of toluene-4-sulphonic acid chloride while cooling with ice and stirring. The thus-obtained thick, cream-colored mass is then stirred for a further 5 hours at 0°-5° C. For the working-up, the mixture is poured on to 420 ml. of ice-water and 140 ml. of concentrated aqueous hydrochloric acid and extracted twice with 300 ml. of ether each time. The extracts are washed twice with water, then with semisaturated aqueous sodium chloride solution and finally with saturated sodium chloride solution dried over sodium sulphate/potassium carbonate and evaporated. There is obtained 1-tosyloxy-3,7,9-trimethyl-6-decene.

Workup

  1. stirringThe thus-obtained thick, cream-colored mass is then stirred for a further 5 hours at 0°-5° C
  2. additionthe mixture is poured on to 420 ml
  3. extractionof concentrated aqueous hydrochloric acid and extracted twice with 300 ml
  4. washThe extracts are washed twice with water
  5. dry with materialwith semisaturated aqueous sodium chloride solution and finally with saturated sodium chloride solution dried over sodium sulphate/potassium carbonate
  6. customevaporated

Sources & evidence

ORD record
ord-5802d2ea1bad4bc4b270a7a38e8eb965
Source dataset
uspto-grants-1977_03
Patent number
US04011335

Reaction notes

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