4-Toluenesulfonyl chloride → HCID 13877995, compound

HRID 1262900Notes

Reaction equation

HRID 1262900 reaction equation
[CH:1]1([OH:8])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:9]1([CH3:19])[CH:14]=[CH:13][C:12]([S:15](Cl)(=[O:17])=[O:16])=[CH:11][CH:10]=1>N1C=CC=CC=1>[C:9]1([CH3:19])[CH:14]=[CH:13][C:12]([S:15]([O:8][CH:1]2[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)(=[O:17])=[O:16])=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 10399Cycloheptanol

Product 1

HCID 13877995HCID 13877995, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

Into a one liter, four-necked, round bottom flask equipped with stirrer, condenser, and thermometer, 200.0 parts of pyridine and 28.5 parts of cycloheptanol were mixed under a nitrogen blanket and chilled to 0° C. with an ice water bath. To this solution 53.5 parts of p-toluenesulfonyl chloride were added in portions over thirty minutes. The solution was stirred for one hour at 0° C. and then allowed stand for twenty-four hours at 15° C. The mixture was poured into one liter of ice water and subsequently extracted with 700 parts of methylene chloride. The organic layer was washed successively with cold 6 N sulfuric acid (until the water layer was acidic to pH paper), dilute sodium bicarbonate (three times with 500 part-portions), and water (twice with 500 part-portions). It was then dried over sodium sulfate, filtered, and the solvent removed in vacuo to yield cycloheptyl para-toluenesulfonate.

Workup

  1. customInto a one liter, four-necked, round bottom flask equipped with stirrer, condenser
  2. customfor twenty-four hours
  3. customat 15° C
  4. extractionsubsequently extracted with 700 parts of methylene chloride
  5. washThe organic layer was washed successively with cold 6 N sulfuric acid (until the water layer
  6. dry with materialIt was then dried over sodium sulfate
  7. filtrationfiltered
  8. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-056d9cd1d9f548c5856dedbf29f1e3d6
Source dataset
uspto-grants-1984_06
Patent number
US04454274

Reaction notes

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