4-Toluenesulfonyl chloride → HCID 20442238, compound

HRID 1632747Notes

Reaction equation

HRID 1632747 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.[CH2:12]([O:20][CH:21]([CH2:24][O:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[CH2:22][OH:23])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]>N1C=CC=CC=1>[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7]([O:23][CH2:22][CH:21]([O:20][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH2:24][O:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])(=[O:9])=[O:8])=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 37244222212-18-6

Product 1

HCID 20442238HCID 20442238, compoundYield 66.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

p-Toluenesulfonyl chloride (1.2 g) was added to a stirred solution of 2,3-di-n-octyloxy-1-propanol (930 mg) in dried pyridine (10 ml) at 2° C. over 7 minutes. The reaction mixture was stirred at 0° to 5° C. for 2 hours and at room temperature overnight. The resultant solution was poured into ice water (50 ml) and extracted with ethyl acetate (40 ml). The extract was washed with dil. hydrochloric acid (20 ml) and a saturated aqueous solution of sodium chloride (20 ml) in turn, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give oil (920 mg) of 2,3-di-n-octyloxy-1-propyl p-toluenesulfonate.

Workup

  1. extractionextracted with ethyl acetate (40 ml)
  2. washThe extract was washed with dil. hydrochloric acid (20 ml)
  3. dry with materiala saturated aqueous solution of sodium chloride (20 ml) in turn, and dried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-a477e2fb8d354451b9a7931e2bb67a30
Source dataset
uspto-grants-1984_10
Patent number
US04477447

Reaction notes

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