4-Toluenesulfonyl chloride → HCID 13463456, compound

HRID 845711Notes

Reaction equation

HRID 845711 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]([CH2:20][CH3:21])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][OH:19]>C1(C)C=CC=CC=1.N1C=CC=CC=1>[CH3:12][C@@H:13]([CH2:20][CH3:21])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][O:19][S:7]([C:4]1[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=1)(=[O:9])=[O:8]

Participants

5

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 5209086-Methyloctan-1-ol

Product 1

HCID 13463456HCID 13463456, compoundYield 87.5%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 1140TolueneSolvent

Procedure

A solution of p-toluenesulfonyl chloride (19.9 g, 0.1 mol) dissolved in toluene (30 ml) was dropwise added with stirring under ice cooling, to a solution of 6-methyloctanol (15.4 g, 0.1 mol) prepared according to the method of a literature (M.C.L.C. 27,417 (1974)) and dissolved in dry pyridine (43 ml), followed by slowly returning the temperature to room temperature, allowing the resulting material to stand overnight, extracting the reaction mixture with toluene after completion of the reaction, washing the resulting organic layer with 6N-hydrochloric acid, then with 2N-NaOH aqueous solution, further with water until the washing water became neutral, drying the layer, and distilling off toluene to obtain oily (S)-6-methyloctyl-p-toluenesulfonate (26.1 g).

Workup

  1. additionwas dropwise added
  2. customprepared
  3. customto room temperature
  4. extractionextracting the reaction mixture with toluene
  5. customafter completion of the reaction
  6. washwashing the resulting organic layer with 6N-hydrochloric acid
  7. customdrying the layer
  8. distillationdistilling off toluene

Sources & evidence

ORD record
ord-27a497d00fd244b28ea2d175da587fe7
Source dataset
uspto-grants-1988_07
Patent number
US04759869

Reaction notes

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