P-Cymene → HCID 22393249, compound

HRID 1953953Notes

Reaction equation

HRID 1953953 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[CH3:5][C:6]1[CH:7]=[CH:8][C:9]([CH:12]([CH3:14])[CH3:13])=[CH:10][CH:11]=1.[C:15](Cl)(=[O:19])[C:16]([CH3:18])=[CH2:17]>C(=S)=S>[CH3:17][CH:16]1[CH2:18][C:10]2[C:11](=[C:6]([CH3:5])[CH:7]=[CH:8][C:9]=2[CH:12]([CH3:14])[CH3:13])[C:15]1=[O:19]

Participants

5

Reactant 3

HCID 7463P-CymeneHCID 13528Methacryloyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 22393249HCID 22393249, compound

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent2×

Procedure

In a 1-liter three-necked flask equipped with a 200 ml dropping funnel were charged 87.61 g (0.66 mol) of anhydrous aluminum chloride and 150 ml of carbon disulfide, to which were added at room temperature through a dropping funnel p-cymene (47.0 ml, 0.301 mol) and methacryloyl chloride (33.0 ml, 0.338 mol) diluted with 30 ml of carbon disulfide. After stirring at room temperature for 5 hours, the reaction mixture was slowly poured on 1 kg of ice. After extraction of the reaction mixture with diethyl ether, the resulting organic layer was washed with an aqueous saturated solution of sodium hydrogen carbonate and with saline, and dried over sodium sulfate. Sodium sulfate was removed by filtration and the solvent was distilled off under reduced pressure.

Workup

  1. customIn a 1-liter three-necked flask equipped with a 200 ml
  2. extractionAfter extraction of the reaction mixture with diethyl ether
  3. washthe resulting organic layer was washed with an aqueous saturated solution of sodium hydrogen carbonate and with saline
  4. dry with materialdried over sodium sulfate
  5. customSodium sulfate was removed by filtration
  6. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-67652aaee9214cc38b5eb659d2c83867
Source dataset
uspto-grants-2000_09
Patent number
US06121182

Reaction notes

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