4-Toluenesulfonyl chloride → HCID 131723944, compound

HRID 1268661Notes

Reaction equation

HRID 1268661 reaction equation
[CH2:1]([OH:5])[CH2:2][CH:3]=[CH2:4].[S:6](Cl)([C:9]1[CH:15]=[CH:14][C:12]([CH3:13])=[CH:11][CH:10]=1)(=[O:8])=[O:7]>N1C=CC=CC=1>[CH2:1]([OH:5])[CH2:2][CH:3]=[CH2:4].[CH3:13][C:12]1[CH:14]=[CH:15][C:9]([S:6]([O-:5])(=[O:8])=[O:7])=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 693893-Buten-1-ol

Product 1

HCID 131723944HCID 131723944, compoundYield 141.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

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).

Workup

  1. extractionextracted with 60 mL diethyl ether
  2. dry with materialdried overnight in the freezer over MgSO4
  3. filtrationThe mixture was filtered
  4. customthe ether evaporated

Sources & evidence

ORD record
ord-453f4023b964490f8e1ef6d001a9b29f
Source dataset
uspto-grants-2007_04
Patent number
US07198915B2

Reaction notes

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