4-Toluenesulfonyl chloride → HCID 21485133, compound

HRID 1414812Notes

Reaction equation

HRID 1414812 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[CH3:12][CH:13]([CH2:18][CH:19]([CH3:21])[CH3:20])[CH2:14][CH:15]([OH:17])[CH3:16]>N1C=CC=CC=1>[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7]([O:17][CH:15]([CH3:16])[CH2:14][CH:13]([CH3:12])[CH2:18][CH:19]([CH3:21])[CH3:20])(=[O:9])=[O:8])=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 5213114,6-Dimethyl-2-heptanol

Product 1

HCID 21485133HCID 21485133, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

9.4 g. of p-toluenesulfonyl chloride are added with ice cooling to a solution of 6.5 g. of 4,6-dimethyl-2-heptanol in 50 ml. of anhydrous pyridine and the mixture is left for 24 hours at 5° C. Thereafter, the mixture is 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 sodium chloride solution, dried over sodium sulfate/potassium carbonate and evaporated at room temperature, finally at 0.05 mmHg. There is obtained 1,3,5-trimethylhexyl p-toluenesulfonate which exhibits a spot in the thin-layer chromatogram [Rf = 0.43; hexane/ethyl acetate (9:1 parts by volume)].

Workup

  1. additionThereafter, the mixture is poured 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 sodium chloride solution
  4. dry with materialdried over sodium sulfate/potassium carbonate
  5. customevaporated at room temperature, finally at 0.05 mmHg

Sources & evidence

ORD record
ord-e53402205a8d4c9c82f401fc7ed7a4f9
Source dataset
uspto-grants-1977_01
Patent number
US04002647

Reaction notes

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