Reaction #1355843

Reaction equation

3-buten-1-ol

Tosyl chloride

→

3-buten-1-ol 4-methylbenzene sulfonate

Yield 141.3%

Solvents

pyridine

Conditions

Workup

1. 1
   Extractionextracted with 60 mL diethyl ether
2. 2
   Dryingdried overnight in the freezer over MgSO4
3. 3
   FiltrationThe mixture was filtered
4. 4
   Otherthe ether evaporated

Procedure

A solution of 3 g (42 mmol) 3-buten-1-ol in 10 mL dry pyridine was cooled in an ice bath. Tosyl chloride (7.9 g, 42 mmol), was added. After stirring for 3 h the mixture was poured into 30 mL of an ice/concentrated HCl 4/1 v/v solution, extracted with 60 mL diethyl ether and dried overnight in the freezer over MgSO4. The mixture was filtered and the ether evaporated to yield 7.22 g (76%) of 3-buten-1-ol 4-methylbenzene sulfonate as a yellow oil. 1H NMR (CDCl3): δ 2.39–2.53 (m, 2H, J=6.5 and 6.9 Hz, CH2—CH═CH2; and s, 3H, CH3—Ar), 4.08 (t, J=6.5 Hz, 2H, CH2OSO2), 5.09–5.15 (m, 2H, JZ=10.4, JE=16.6, Jgem=3.1 Hz, CH2—CH═CH2), 5.57–5.82 (m, 1H, JZ=10.4, JE=16.6, J=6.9 Hz, CH2—CH═CH2), 7.38 and 7.72 (d,4H, J=8.6 Hz, Ar).

Source