Succinyl chloride → HCID 18704184, compound

HRID 2288256Notes

Reaction equation

HRID 2288256 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[OH:9].[C:10](Cl)(=[O:16])[CH2:11][CH2:12][C:13](Cl)=[O:14].[Cl-].[Al+3].[Cl-].[Cl-]>C(Cl)Cl>[CH3:1][C:2]1[CH:7]=[C:6]([C:10](=[O:16])[CH2:11][CH2:12][C:13]([C:6]2[CH:5]=[C:4]([CH3:8])[C:3]([OH:9])=[C:2]([CH3:1])[CH:7]=2)=[O:14])[CH:5]=[C:4]([CH3:8])[C:3]=1[OH:9]

Participants

5

Reactant 3

HCID 10970Succinyl chlorideHCID 113352,6-DimethylphenolHCID 6451240Aluminum(III) Chloride2×

Product 1

HCID 18704184HCID 18704184, compoundYield 15.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 300 ml of methylene chloride was dissolved 10 g/82 mmol of 2,6-dimethylphenol and 6.2 g/40 mmol of succinic dichloride, and the solution was cooled to 0° C. in sodium chloride-ice bath. 49 g/368 mmol of anhydrous aluminum chloride was added dropwise to the mixture with thorough stirring while maintaining the temperature to not more than 5° C. After completing the addition, the mixture was stirred at 5° C. for one hour, and at room temperature for 15 hours. The reaction mixture was then added to 50 ml of ice containing conc. hydrochloric acid to decompose excessive anhydrous aluminum chloride, and the mixture was extracted twice with methylene chloride. The organic layer was washed with saturated sodium chloride solution, and dried with anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was recrystalized from toluene to obtain 2.0 g of 1,4-bis(3',5'-dimethyl-4'-hydroxyphenyl)butane-1,4-dione. MS: 326 (M+).

Workup

  1. temperaturewhile maintaining the temperature to not more than 5° C
  2. additionthe addition
  3. stirringthe mixture was stirred at 5° C. for one hour
  4. extractionthe mixture was extracted twice with methylene chloride
  5. washThe organic layer was washed with saturated sodium chloride solution
  6. dry with materialdried with anhydrous sodium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe residue was recrystalized from toluene

Sources & evidence

ORD record
ord-abb5a355e71148c1acbe191d00fc48cd
Source dataset
uspto-grants-2000_07
Patent number
US06087502

Reaction notes

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