4-Toluenesulfonyl chloride → HCID 58597012, compound

HRID 2220053Notes

Reaction equation

HRID 2220053 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.[CH:12]1([OH:18])[CH2:16][CH2:15][CH:14]([OH:17])[CH2:13]1>ClCCl.N1C=CC=CC=1>[CH3:11][C:1]1[CH:6]=[CH:5][C:4]([S:7]([O:17][CH:14]2[CH2:15][CH2:16][CH:12]([OH:18])[CH2:13]2)(=[O:9])=[O:8])=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 100165Cyclopentane-1,3-diol

Product 1

HCID 58597012HCID 58597012, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent3×

Conditions

Temperature
15 °C

Procedure

A solution of 9.00 g p-toluenesulphonic acid chloride in 30 ml dichloromethane is added dropwise to an ice-cooled solution of 4.97 g cyclopentan-1,3-diol (cis/trans mixture) in 15 ml of pyridine and 10 ml dichloromethane. The solution is stirred for 45 min at 15° C. The solution is diluted with 100 ml dichloromethane, washed twice with 2 N hydrochloric acid and once with water. After drying through sodium sulphate and elimination of the solvent the product is obtained as a brown oil.

Workup

  1. washwashed twice with 2 N hydrochloric acid and once with water
  2. dry with materialAfter drying through sodium sulphate and elimination of the solvent the product
  3. customis obtained as a brown oil

Sources & evidence

ORD record
ord-a9d102cbb4cb452caf9afe823534d62a
Source dataset
uspto-grants-2008_08
Patent number
US07417032B2

Reaction notes

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