Chloral → Chloral dimethylketene

HRID 1579933Notes

Reaction equation

HRID 1579933 reaction equation
CC(C)([O-])C.[Li+].[O:7]=[CH:8][C:9]([Cl:12])([Cl:11])[Cl:10].[CH3:13][C:14]([CH3:17])=[C:15]=[O:16]>C1CCCCC1>[O:7]=[CH:8][C:9]([Cl:12])([Cl:11])[Cl:10].[CH3:13][C:14]([CH3:17])=[C:15]=[O:16]

Participants

5

Reactant 3

HCID 6407ChloralHCID 1363951-Propen-1-one, 2-methyl-HCID 236647642-Propanol, 2-methyl-, lithium salt (1:1)

Product 1

HCID 86732904Chloral dimethylketene

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Conditions

Temperature
60 °C

Procedure

In a 50 ml. glass polymerization tube was placed a sealed vial containing 0.2 ml. of a 2 molar solution of lithium tert-butoxide in cyclohexane and several steel balls. Chloral (30 g.) was added to the tube and dimethylketene (1.2 g.) was then condensed into the tube. The supernatant air in the tube was evacuated after which the tube was sealed and heated to 60°C. The tube was shaken vigorously to cause the steel balls to break the vial containing the initiator and to produce a homogeneous solution. After the contents of the tube had come to rest it was placed without agitation in a -30°C. bath. Polymerization commenced in the placid mixture almost immediately. The tube was taken out after an hour and the polymerization was allowed to go to completion overnight at room temperature. The initial yellow color of the solution almost completely disappeared during the polymerization. The tube was opened and a tough and stiff chloral-dimethylketene copolymer was obtained. Elemental analysis for carbon and hydrogen indicated the polymer contained 6% of dimethylketene, and the infrared spectrum of the polymer showed a strong ester band at 5.75 μ.

Workup

  1. customglass polymerization tube
  2. additionvial containing 0.2 ml
  3. customcondensed into the tube
  4. customThe supernatant air in the tube was evacuated after which the tube
  5. customwas sealed
  6. additioncontaining the initiator
  7. customto produce a homogeneous solution
  8. customwas placed without agitation in a -30°C.
  9. customPolymerization
  10. waitThe tube was taken out after an hour
  11. customto go to completion overnight at room temperature
  12. customThe initial yellow color of the solution almost completely disappeared during the polymerization

Sources & evidence

ORD record
ord-69f519c878f54a04ae2e5eb932c6bd5b
Source dataset
uspto-grants-1976_01
Patent number
US03932318

Reaction notes

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