3-Chloro-2-chloromethyl-1-propene → HCID 11096855, compound

HRID 1978103Notes

Reaction equation

HRID 1978103 reaction equation
[Cl:1][CH2:2][C:3]([CH2:5]Cl)=[CH2:4].[C:7]1([CH3:16])[CH:12]=[CH:11][C:10]([S:13]([O-:15])=[O:14])=[CH:9][CH:8]=1.[Na+]>CO>[Cl:1][CH2:2][C:3]([CH2:5][S:13]([C:10]1[CH:11]=[CH:12][C:7]([CH3:16])=[CH:8][CH:9]=1)(=[O:15])=[O:14])=[CH2:4]

Participants

4

Reactant 2

HCID 158593-Chloro-2-chloromethyl-1-propeneHCID 2723791Sodium p-toluenesulfinate

Product 1

HCID 11096855HCID 11096855, compoundYield 44.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2-(chloromethyl)-3-chloropropene (3.13 g, 25 mmol) and sodium p-toluenesulfmate (4.60 g, 25 mmol) in methanol (50 mL) was heated under reflux for 24 hours. The solvent was evaporated on a rotary evaporator and the residue was extracted between dichloromethane and water. The organic layer was dried (anhydrous MgSO4) and evaporated to give crude product (4.7 g) which, after purification by column chromatography on a silica-gel column using ethyl acetate/n-hexane 1:9 as eluent, gave pure product (2.7 g, 44% yield). 1H-NMR (CDCl3) δ (ppm): 2.46 (s, 3H, CH3Ar); 3.92 (s, 2H, CH2SO2); 4.19 (s, 2H, CH2Cl); 5.02 (s, 1H, vinylic-H); 5.45 (s, 1H, vinylic-H); 7.37 and 7.77 (2d, 4H, ArH).

Workup

  1. temperatureunder reflux for 24 hours
  2. customThe solvent was evaporated on a rotary evaporator
  3. extractionthe residue was extracted between dichloromethane and water
  4. dry with materialThe organic layer was dried (anhydrous MgSO4)
  5. customevaporated
  6. customto give crude product (4.7 g) which
  7. customafter purification by column chromatography on a silica-gel column

Sources & evidence

ORD record
ord-756ebad2722848af92a7255ad40cced4
Source dataset
uspto-grants-2001_05
Patent number
US06235857B1

Reaction notes

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