Hydrochloric Acid → 4-Penten-2-ol p-toluenesulfonate

HRID 382465Notes

Reaction equation

HRID 382465 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.[CH3:12][CH:13]([OH:17])[CH2:14][CH:15]=[CH2:16].Cl>N1C=CC=CC=1>[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7]([O:17][CH:13]([CH2:14][CH:15]=[CH2:16])[CH3:12])(=[O:9])=[O:8])=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 122474-Penten-2-OL

Product 1

HCID 126034754-Penten-2-ol p-toluenesulfonate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
3.5 °C

Procedure

Under a nitrogen atmosphere, p-toluenesulfonyl chloride (16.92 g, 88.75 mmol) was added to a cold (2° C.), stirring solution of 4-penten-2-ol (7.28 g, 84.52 mmol, Aldrich Chemical Company) in pyridine (60 mL). The solution was stirred at 2-5° C. for 2 h and allowed to warm to ambient temperature over several hours. The mixture, containing white solids, was poured into cold 3 M HCl solution (250 mL) and extracted with CHCl3 (4×75 mL). The combined CHCl3 extracts were washed with 3 M HCl solution (4×100 mL), saturated NaCl solution (2×50 mL), dried (Na2SO4), filtered, concentrated on a rotary evaporator, and further dried under high vacuum to afford 17.38 g (85.6%) of a light-amber oil.

Workup

  1. temperatureto warm to ambient temperature over several hours
  2. additionThe mixture, containing white solids
  3. extractionextracted with CHCl3 (4×75 mL)
  4. washThe combined CHCl3 extracts were washed with 3 M HCl solution (4×100 mL), saturated NaCl solution (2×50 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated on a rotary evaporator
  8. customfurther dried under high vacuum
  9. customto afford 17.38 g (85.6%) of a light-amber oil

Sources & evidence

ORD record
ord-6dd3ba38694544ce89c6f9be4f37f640
Source dataset
uspto-grants-2001_10
Patent number
US06310102B1

Reaction notes

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