Hydrochloric Acid → HCID 86740223, compound

HRID 649486Notes

Reaction equation

HRID 649486 reaction equation
[CH2:1]=[CH:2][CH:3]=[CH2:4].[Cl-].[Al+3].[Cl-].[Cl-].[Cl-].[Al+3].[Cl-].[Cl-].[CH2:13]([O:17][C:18](=[O:21])[CH:19]=[CH2:20])[CH2:14][CH2:15][CH3:16].Cl>O>[CH2:1]=[CH:2][CH:3]=[CH2:4].[CH2:13]([O:17][C:18](=[O:21])[CH:19]=[CH2:20])[CH2:14][CH2:15][CH3:16]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 78451,3-Butadiene2×HCID 6451240Aluminum(III) Chloride2×HCID 86742115HCID 86742115, compound

Product 1

HCID 86740223HCID 86740223, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The adduct of butadiene-butylacrylate was prepared by charging 513 grams (4 moles) of butadiene-1,3 to a two-liter flask fitted with a stirrer, reflux condenser, and nitrogen inlet tube. To the butadiene is added 50.4 grams of aluminum chloride (AlCl3) over a one-minute period while stirring the reaction mixture at a temperature within the range of 25°-28° C. A colorless clear solution resulted. The butadiene was blown into the aluminum chloride-butylacrylate mixture over a 1.75 hour period while maintaining the reaction mass at a temperature of 28°-59° C. Then the reaction mass is stirred for two hours while maintaining the temperature within the range of 41°-52° C. followed by the addition of a solution of 150 mililiters of concentrated hydrochloric acid and 1000 grams of water to the reaction mass to hydrolyze the aluminum chloride. The resulting aqueous phase of the reaction mass is discarded. The organic phase is washed with 1000 mililiters of water at 40° C. and the resulting aqueous phase is discarded leaving the organic phase at the desired adduct weighing 735 grams.

Workup

  1. customfitted with a stirrer
  2. temperaturereflux condenser, and nitrogen inlet tube
  3. customA colorless clear solution resulted
  4. temperaturewhile maintaining the reaction mass at a temperature of 28°-59° C
  5. stirringThen the reaction mass is stirred for two hours
  6. temperaturewhile maintaining the temperature within the range of 41°-52° C.
  7. washThe organic phase is washed with 1000 mililiters of water at 40° C.

Sources & evidence

ORD record
ord-668ec220ba2e476599494429d25015ed
Source dataset
uspto-grants-1988_04
Patent number
US04740322

Reaction notes

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