4-Toluenesulfonyl chloride → HCID 54140460, compound

HRID 1414817Notes

Reaction equation

HRID 1414817 reaction equation
[CH3:1][CH:2]([CH2:6][CH2:7][CH2:8][C:9]([CH3:13])([O:11][CH3:12])[CH3:10])[CH2:3][CH2:4][OH:5].[CH3:14][C:15]1[CH:20]=[CH:19][C:18]([S:21](Cl)(=[O:23])=[O:22])=[CH:17][CH:16]=1>N1C=CC=CC=1>[C:15]1([CH3:14])[CH:20]=[CH:19][C:18]([S:21]([O:5][CH2:4][CH2:3][CH:2]([CH3:1])[CH2:6][CH2:7][CH2:8][C:9]([CH3:13])([O:11][CH3:12])[CH3:10])(=[O:23])=[O:22])=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 1700411-Octanol, 7-methoxy-3,7-dimethyl-

Product 1

HCID 54140460HCID 54140460, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3.76 g. of 3,7-dimethyl-7-methoxy-1-octanol are dissolved in 20 ml. of anhydrous pyridine and mixed, while stirring and with ice cooling, with 4.2 g. of p-toluenesulfochloride. Subsequently, the solution is left overnight at 5° C., then poured onto ice-water and extracted three times with diethyl ether. The extracts are washed successively with cold 2-N aqueous hydrochloric acid solution, water and twice with saturated aqueous sodium chloride solution, dried over sodium sulfate/potassium carbonate and evaporated under reduced pressure, finally at 0.05 mmHg. There is obtained 3,7-dimethyl-7-methoxy-octyl p-toluenesulfonate; nD20 = 1.4927.

Workup

  1. additionpoured onto ice-water
  2. extractionextracted three times with diethyl ether
  3. washThe extracts are washed successively with cold 2-N aqueous hydrochloric acid solution, water and twice with saturated aqueous sodium chloride solution
  4. dry with materialdried over sodium sulfate/potassium carbonate
  5. customevaporated under reduced pressure, finally at 0.05 mmHg

Sources & evidence

ORD record
ord-906af1570e3445b9b459e5578282528e
Source dataset
uspto-grants-1977_01
Patent number
US04002647

Reaction notes

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