Hydrochloric Acid → 6-Pentyloxyheptyl p-toluenesulfonate

HRID 1885126Notes

Reaction equation

HRID 1885126 reaction equation
[CH2:1]([O:6][CH:7]([CH3:14])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][OH:13])[CH2:2][CH2:3][CH2:4][CH3:5].[C:15]1([CH3:25])[CH:20]=[CH:19][C:18]([S:21](Cl)(=[O:23])=[O:22])=[CH:17][CH:16]=1.Cl>N1C=CC=CC=1.O>[C:15]1([CH3:25])[CH:20]=[CH:19][C:18]([S:21]([O:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH:7]([O:6][CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])[CH3:14])(=[O:23])=[O:22])=[CH:17][CH:16]=1

Participants

6

Reactant 3

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

Product 1

HCID 233663776-Pentyloxyheptyl p-toluenesulfonateYield 82.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

In a solution of 3 g of 6-pentyloxyheptanol in 10 ml of pyridine, 3.4 g of p-toluenesulfonyl chloride was added in 30 min. at 0°-5° C. After the addition, the mixture was stirred for 5 hours at an increased temperature of 20°-25° C. After the reaction, the mixture was poured in cold water, acidified with 6N-hydrochloric acid and extracted with ethyl acetate. The extract was washed with water and dried with anhydrous MgSO4, followed by distilling-off of the ethyl acetate to obtain 4.36 g of 6-pentyloxyheptyl p-toluenesulfonate.

Workup

  1. additionAfter the addition
  2. customAfter the reaction
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with water
  5. dry with materialdried with anhydrous MgSO4

Sources & evidence

ORD record
ord-907f53101aef454888c0aeedb215cf0f
Source dataset
uspto-grants-1992_09
Patent number
US05143643

Reaction notes

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