1,1-Dichloro-2,2-diethoxyethane → Chloroketene diethylacetal

HRID 1769060Notes

Reaction equation

HRID 1769060 reaction equation
[CH2:1]([O:3][CH:4]([O:8][CH2:9][CH3:10])[CH:5](Cl)[Cl:6])[CH3:2].CC(C)([O-])C.[K+]>C1COCC1>[Cl:6][CH:5]=[C:4]([O:8][CH2:9][CH3:10])[O:3][CH2:1][CH3:2]

Participants

4

Reactant 2

HCID 120801,1-Dichloro-2,2-diethoxyethaneHCID 23665647Potassium tert-butoxide

Product 1

HCID 6451889Chloroketene diethylacetalYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of dichloroacetaldehyde diethylacetal (25 g; 0.1336 mol) in 150 ml of THF cooled to 0° C. was added 17.99 g (0.16 mol) of potassium t-butoxide in 50 ml of THF. The ice-bath was removed, and the reaction mixture was allowed to reflux for 16 hr and cooled. The reaction mixture was filtered (through celite) and a pale yellow solution was concentrated in vacuo at 30° C. The residue was distilled to afford 18.1 g (90%) of 2-chloro-1,1-diethoxyethylene (Formula V: R3 =Cl; R4 =H; R5 =R6 =OC2H5), a colorless liquid, b.p. 70°-76° C./20-25 mm.

Workup

  1. customThe ice-bath was removed
  2. temperatureto reflux for 16 hr
  3. temperaturecooled
  4. filtrationThe reaction mixture was filtered (through celite)
  5. concentrationa pale yellow solution was concentrated in vacuo at 30° C
  6. distillationThe residue was distilled

Sources & evidence

ORD record
ord-d57971863345404fbfa30e2a65cd833f
Source dataset
uspto-grants-1995_01
Patent number
US05380729

Reaction notes

Loading…