Hydrochloric Acid → 6-Pentyloxyheptyl p-toluenesulfonate

HRID 1079277Notes

Reaction equation

HRID 1079277 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:17][CH:18]([CH3:25])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][OH:24])[CH2:13][CH2:14][CH2:15][CH3:16].O.Cl>N1C=CC=CC=1>[CH2:12]([O:17][CH:18]([CH3:25])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][O:24][S:7]([C:4]1[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=1)(=[O:9])=[O:8])[CH2:13][CH2:14][CH2:15][CH3:16]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 23366378HCID 23366378, compound

Product 1

HCID 233663776-Pentyloxyheptyl p-toluenesulfonateYield 82.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

A solution of 2.26 g of p-toluenesulfonic acid chloride in 5 ml of pyridine was gradually added dropwise to a cooled solution of 2.04 g of 6-pentyloxyheptanol in 8 ml of pyridine for 7 min. below 5° C. After stirring for 5 hours at room temperature, the reaction mixture was injected into 150 ml of cold water and, after being acidified to pH 3 with 6N-hydrochloric acid, was extracted with ethyl acetate. The resultant solution was washed with water and dried with anhydrous magnesium sulfate, followed by distilling-off of the solvent to obtain 2.98 g of (6-pentyloxyheptyl)-p-toluenesulfonate.

Workup

  1. extractionwas extracted with ethyl acetate
  2. washThe resultant solution was washed with water
  3. dry with materialdried with anhydrous magnesium sulfate

Sources & evidence

ORD record
ord-54fa65e2709b496fb61caff34a76b847
Source dataset
uspto-grants-1996_12
Patent number
US05580489

Reaction notes

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