Water → 2-(Chloromethylidene)-3,3-dimethyloxolane

HRID 2164899Notes

Reaction equation

HRID 2164899 reaction equation
[Cl:1][C:2](Cl)=[CH:3][C:4]([CH3:9])([CH3:8])[CH2:5][CH2:6]Cl.C([O-])(=[O:13])C.[Na+].C[O-].[Na+].O>CN(C)C=O.CO>[Cl:1][CH:2]=[C:3]1[C:4]([CH3:9])([CH3:8])[CH2:5][CH2:6][O:13]1

Participants

7

Reactant 4

HCID 962WaterHCID 517045Sodium AcetateHCID 10942334Sodium MethoxideHCID 155843271,1,5-Trichloro-3,3-dimethylpent-1-ene

Product 1

HCID 536634572-(Chloromethylidene)-3,3-dimethyloxolaneYield 89%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

806 g (4 mols) of 1,1,5-trichloro-3,3-dimethyl-1-pentene are heated under reflux for 6 hours together with 360 g (4.4 mols) of anhydrous sodium acetate in 1 liter of dimethylformamide. When the reaction mixture has cooled down to about 100°, 1.6 liters (8 mols) of 30% sodium methylate solution in methanol are added dropwise, and the mixture is heated under reflux for a further 4 hours. The cold solution is poured into water, and the mixture is repeatedly extracted with methylene chloride. When the solution has been dried and the solvent driven off, 654 g of product remain which are fractionated over a column. 522 g (3.56 mols, 89%) of 2-chloromethylene-3,3-dimethyltetrahydrofuran are obtained with a boiling point of 84°-87°/20.

Workup

  1. temperatureWhen the reaction mixture has cooled down to about 100°
  2. temperaturethe mixture is heated
  3. temperatureunder reflux for a further 4 hours
  4. extractionthe mixture is repeatedly extracted with methylene chloride
  5. customWhen the solution has been dried

Sources & evidence

ORD record
ord-8f372464c1fe4326b0305dc287e380e3
Source dataset
uspto-grants-1985_03
Patent number
US04507496

Reaction notes

Loading…