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

HRID 1282237Notes

Reaction equation

HRID 1282237 reaction equation
[S:1](Cl)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].[CH3:12][CH:13]([OH:17])[CH2:14][CH:15]=[CH2:16].Cl>N1C=CC=CC=1>[C:7]1([CH3:8])[CH:9]=[CH:10][C:4]([S:1]([O:17][CH:13]([CH2:14][CH:15]=[CH2:16])[CH3:12])(=[O:3])=[O:2])=[CH:5][CH:6]=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, tosyl 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) 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-03fae9cbb504424697b4e2a763ff3767
Source dataset
uspto-grants-2002_09
Patent number
US06455554B1

Reaction notes

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