Hydrochloric Acid → HCID 19880027, compound

HRID 1885122Notes

Reaction equation

HRID 1885122 reaction equation
[CH2:1]([O:6][CH:7]([CH3:11])[CH2:8][CH2:9][OH:10])[CH2:2][CH2:3][CH2:4][CH3:5].[C:12]1([CH3:22])[CH:17]=[CH:16][C:15]([S:18](Cl)(=[O:20])=[O:19])=[CH:14][CH:13]=1.[OH-].[Na+].Cl>C1C=CC=CC=1.N1C=CC=CC=1>[C:12]1([CH3:22])[CH:17]=[CH:16][C:15]([S:18]([O:10][CH2:9][CH2:8][CH:7]([O:6][CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])[CH3:11])(=[O:20])=[O:19])=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 19880018HCID 19880018, compound

Product 1

HCID 19880027HCID 19880027, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 1049PyridineSolvent

Procedure

5.0 g of 3-pentyloxybutanol, 3.98 g of p-toluenesulfonyl chloride, 1.65 g of pyridine, and 8 ml of benzene were charged in a 30 ml-reaction vessel and, under N2 stream, stirred for 23 hours at room temperature. Then, into the reaction mixture, 6.3 ml of hot conc. NaOH aqueous solution was added and stirred for 5 min. The mixture was poured in 280 ml of cold 10%-hydrochloric acid solution and extracted with hexane. The hexane layer was washed successively with cold 5%-hydrochloric acid solution, saturated NaCO3 aqueous solution and water and dried with anhydrous MgSO4, followed by distilling-off of the solvent to 6.0 g of a crude product, which was purified by alumina column chromatography (hexane) to obtain 2.3 g of 3-pentyloxybutyl p-toluenesulfonate.

Workup

  1. stirringstirred for 5 min
  2. extractionextracted with hexane
  3. washThe hexane layer was washed successively with cold 5%-hydrochloric acid solution, saturated NaCO3 aqueous solution and water
  4. dry with materialdried with anhydrous MgSO4
  5. customwas purified by alumina column chromatography (hexane)

Sources & evidence

ORD record
ord-e612e84157bb4ef7a469a7fe0e4c7b1b
Source dataset
uspto-grants-1992_09
Patent number
US05143643

Reaction notes

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