Hydrochloric Acid → HCID 19880051, compound

HRID 1885123Notes

Reaction equation

HRID 1885123 reaction equation
[CH2:1]([O:9][CH:10]([CH3:15])[CH2:11][CH2:12][CH2:13][OH:14])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[C:16]1([CH3:26])[CH:21]=[CH:20][C:19]([S:22](Cl)(=[O:24])=[O:23])=[CH:18][CH:17]=1.[OH-].[Na+].Cl>C1C=CC=CC=1.N1C=CC=CC=1>[C:16]1([CH3:26])[CH:21]=[CH:20][C:19]([S:22]([O:14][CH2:13][CH2:12][CH2:11][CH:10]([O:9][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])[CH3:15])(=[O:24])=[O:23])=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 19880048HCID 19880048, compound

Product 1

HCID 19880051HCID 19880051, compoundYield 78.2%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 1049PyridineSolvent

Procedure

7 g of 4-octyloxypentanol, 4.34 g of p-toluenesulfonyl chloride, 1.8 g of pyridine and 10 ml of benzene were stirred under N2 stream at room temperature for 22 hours. Thereafter, 6.5 ml of hot conc. NaOH aqueous solution was added to the reaction mixture and stirred for 5 min. Then, the mixture was poured into cold 10%-hydrochloric acid and extracted with hexane. The hexane layer was washed successively with cold 5%-hydrochloric acid, saturated NaHCO3 aqueous solution and water and dried with anhydrous MgSO4. After removing the solvent by distillation, the product was treated with alumina column (hexane) to obtain 6.6 g of 4-octyloxypentyl p-toluenesulfonate.

Workup

  1. extractionextracted with hexane
  2. washThe hexane layer was washed successively with cold 5%-hydrochloric acid, saturated NaHCO3 aqueous solution and water
  3. dry with materialdried with anhydrous MgSO4
  4. customAfter removing the solvent
  5. distillationby distillation
  6. additionthe product was treated with alumina column (hexane)

Sources & evidence

ORD record
ord-dcadc74a87a74636a82ce6f790f5cf9b
Source dataset
uspto-grants-1992_09
Patent number
US05143643

Reaction notes

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