Hydrochloric Acid → Hexyl p-Toluenesulfonate

HRID 892381

Reaction equation

HRID 892381 reaction equation
N1C=CC=CC=1.[CH2:7]([OH:13])[CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[C:14]1([CH3:24])[CH:19]=[CH:18][C:17]([S:20](Cl)(=[O:22])=[O:21])=[CH:16][CH:15]=1.Cl>O>[C:14]1([CH3:24])[CH:19]=[CH:18][C:17]([S:20]([O:13][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])(=[O:22])=[O:21])=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 81031-Hexanol

Product 1

HCID 220448Hexyl p-ToluenesulfonateYield 95.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

20 ml of pyridine was added to 5.02 g (49.2 mM) of n-hexanol, followed by stirring below 0° C. To the mixture, 11.24 g (59.0 mM) of p-toluenesulfonyl chloride was added. The mixture was stirred for 6 hours below 0° C. After the reaction, the reaction mixture was poured into iced water and acidified with conc. HCl, followed by two times of extraction with dichloromethane, two times of washing with water, drying with sodium sulfate and distilling-off of the solvent to obtain 12.0 g (46.8 mM) of an objective product (yield: 95.0%).

Workup

  1. stirringThe mixture was stirred for 6 hours below 0° C
  2. customAfter the reaction
  3. extractionfollowed by two times of extraction with dichloromethane, two times
  4. washof washing with water
  5. dry with materialdrying with sodium sulfate and distilling-off of the solvent

Sources & evidence

ORD record
ord-1db238807f724e3bb3f67050f755e667
Source dataset
uspto-grants-1992_06
Patent number
US05118441

Linked notes

Loading…