2,6-Dimethylphenol → HCID 18704166, compound

HRID 2288255Notes

Reaction equation

HRID 2288255 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[OH:9].[Cl-].[Al+3].[Cl-].[Cl-].[C:14](Cl)(=[O:22])[CH2:15][CH2:16][CH2:17][CH2:18][C:19](Cl)=[O:20]>C(Cl)Cl>[CH3:1][C:2]1[CH:7]=[C:6]([C:14](=[O:22])[CH2:15][CH2:16][CH2:17][CH2:18][C:19]([C:6]2[CH:5]=[C:4]([CH3:8])[C:3]([OH:9])=[C:2]([CH3:1])[CH:7]=2)=[O:20])[CH:5]=[C:4]([CH3:8])[C:3]=1[OH:9]

Participants

5

Reactant 3

HCID 113352,6-DimethylphenolHCID 61034Adipoyl chlorideHCID 6451240Aluminum(III) Chloride2×

Product 1

HCID 18704166HCID 18704166, compoundYield 17.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To 300 ml of methylene chloride was dissolved 10 g/82 mmol of 2,6-dimethylphenol, and the solution was cooled to 0° C. in sodium chloride-ice bath. After adding 49 g/368 mmol of anhydrous aluminum chloride, methylene chloride solution of 7.3 g/40 mmol of adipic dichloride was added dropwise to the mixture with thorough stirring while maintaining the temperature to not more than 5° C. The reaction mixture was 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 2.5 g of 1,6-bis(3',5'-dimethyl-4'-hydroxyphenyl)hexane-1,6-dione. MS: 354 (M+).

Workup

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

Sources & evidence

ORD record
ord-000eac1e03824f4fba45c173a8a28604
Source dataset
uspto-grants-2000_07
Patent number
US06087502

Reaction notes

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