Acetone → HCID 11320947, compound

HRID 426892Notes

Reaction equation

HRID 426892 reaction equation
[H-].[K+].[CH3:3][C:4]([CH3:6])=[O:5].[C:7](Cl)(=[O:11])[CH:8]([CH3:10])[CH3:9].O>O1CCCC1>[C:7]([O:5][C:4]([CH3:6])=[CH2:3])(=[O:11])[CH:8]([CH3:10])[CH3:9]

Participants

6

Reactant 4

HCID 180Acetone2×HCID 962WaterHCID 62325Isobutyryl chloride2×HCID 82127Potassium hydride2×

Product 1

HCID 11320947HCID 11320947, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-10 °C

Procedure

Isopropenyl isobutyrate was prepared by the potassium hydride catalyzed condensation of acetone with isobutyryl chloride as follows. A suspension of potassium hydride (100 g, 2.5 mol.) in 1.5 liters of dry tetrahydrofuran was prepared. The suspension was cooled to -10° C. and 200 ml acetone was slowly added maintaining the temperature of the reaction mixture between 0° and -10° C. The resulting solution of acetone enolate was added to a solution of 266 g (2.5 mol.) of isobutyryl chloride in 3 liters of tetrahydrofuran over a 30-minute period. The temperature of the reaction flask was maintained between -30° and -50° C. during the addition. After 16 hours the reaction mixture was poured into water and the resulting mixture was extracted with ether. The ether extracts were combined, dried over sodium sulfate, and the solvent was removed. The residue was distilled through a thin film evaporator (114° to 125° C.) and the distillate was redistilled through a spinning band column. The fraction boiling at 40° to 46° C. (1.5 mm Hg) was collected to give a total of 21 g (7%) of pure isopropenyl isobutyrate. The isopropenyl isobutyrate was polymerized according to the method described in Example 2 to give the corresponding polymer.

Workup

  1. customwas prepared
  2. temperaturemaintaining the temperature of the reaction mixture between 0° and -10° C
  3. temperatureThe temperature of the reaction flask was maintained between -30° and -50° C. during the addition
  4. extractionthe resulting mixture was extracted with ether
  5. dry with materialdried over sodium sulfate
  6. customthe solvent was removed
  7. distillationThe residue was distilled through a thin film evaporator (114° to 125° C.)
  8. distillationthe distillate was redistilled through a spinning band column
  9. customThe fraction boiling at 40° to 46° C. (1.5 mm Hg) was collected

Sources & evidence

ORD record
ord-93bb6dc882354a659557ac726edad687
Source dataset
uspto-grants-1979_10
Patent number
US04171702

Reaction notes

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