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

HRID 1253277Notes

Reaction equation

HRID 1253277 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

Conditions

Temperature
100 °C

Procedure

806 g (4 moles) of 1,1,5-trichloro-3,3-dimethyl-1-pentene are heated under reflux with 360 g (4.4 moles) of anhydrous sodium acetate in 1 liter of dimethylformamide for 6 hours. After cooling to about 100° C., 1.6 liters (8 moles) of 30% strength 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 extracted several times with methylene chloride. After the solution has been dried and the solvent has been distilled off, 654 g of product remain, and are fractionated over a column. 522 g (80% of theory) of 2-chloromethylene-3,3-dimethyl-tetrahydrofuran of boiling point 84°-87° C./20 mbar are obtained.

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for a further 4 hours
  3. extractionextracted several times with methylene chloride
  4. customAfter the solution has been dried
  5. distillationthe solvent has been distilled off

Sources & evidence

ORD record
ord-1a682635deeb424d889c2f74755cc054
Source dataset
uspto-grants-1988_05
Patent number
US04748249

Reaction notes

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