Methylsuccinic anhydride → HCID 14234796, compound

HRID 1614029Notes

Reaction equation

HRID 1614029 reaction equation
[CH3:1][C:2]1([CH3:14])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH3:13])([CH3:12])[CH2:4][CH2:3]1.[CH3:15][CH:16]1[CH2:21][C:20](=[O:22])[O:19][C:17]1=[O:18].[Cl-].[Al+3].[Cl-].[Cl-]>ClCCCl>[CH3:1][C:2]1([CH3:14])[CH2:3][CH2:4][C:5]([CH3:13])([CH3:12])[C:6]2[CH:7]=[C:8]([C:20](=[O:22])[CH2:21][CH:16]([CH3:15])[C:17]([OH:19])=[O:18])[CH:9]=[CH:10][C:11]1=2

Participants

5

Reactant 3

HCID 20051Methylsuccinic anhydrideHCID 811861,1,4,4-TetramethyltetralinHCID 6451240Aluminum(III) Chloride

Product 1

HCID 14234796HCID 14234796, compoundYield 34.2%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 37.7 g (0.2 mole) of 1,1,4,4-tetramethyl1,2,3,4-tetrahydro naphthalene and 22.82 g (0.2 mole) of methylsuccinic anhydride in 250 cm3 of anhydrous 1,2-dichloroethane, there are added, by portions, over a period of about 1 hour, 53.3 g (0.4 mole) of anhydrous aluminum chloride in a manner to maintain the temperature lower than or equal to 30° C. After stirring for 3 hours at ambient temperature, the reaction mixture is poured into 200 cm3 of ice water. The organic phase is decanted. The aqueous phase is again extracted twice with 100 cm3 of dichloromethane. The dichloroethane and dichloromethane phases are combined, washed with water, dried on sodium sulfate and concentrated under reduced pressure. The residue is taken up in 300 cm3 of hexane, filtered, successively washed three times with 200 cm3 of toluene and then recrystallized in isopropyl ether. After drying, 20.7 g of 4-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro- 2-naphthyl) -4-oxo-2-methyl butyric acid in the form of a white solid whose melting point is 165° C. are obtained.

Workup

  1. customThe organic phase is decanted
  2. extractionThe aqueous phase is again extracted twice with 100 cm3 of dichloromethane
  3. washwashed with water
  4. customdried on sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. filtrationfiltered
  7. washsuccessively washed three times with 200 cm3 of toluene
  8. customrecrystallized in isopropyl ether
  9. customAfter drying

Sources & evidence

ORD record
ord-f36d47e9bd594de7b55bac4c47674fc1
Source dataset
uspto-grants-1993_03
Patent number
US05194663

Reaction notes

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