2-Acetylhydroquinone → HCID 11322818, compound

HRID 1153702Notes

Reaction equation

HRID 1153702 reaction equation
[C:1]([C:4]1[CH:10]=[C:9]([OH:11])[CH:8]=[CH:7][C:5]=1[OH:6])(=[O:3])[CH3:2].S([O-])([O-])(=O)=O.[Ca+2]>C(OCC)(=O)C.C(#N)C.C(O)C1C=CC=CC=1>[C:1]([C:4]1[C:5](=[O:6])[CH:7]=[CH:8][C:9](=[O:11])[C:10]=1[O:3][CH2:1][C:4]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:5]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 2

HCID 102792-AcetylhydroquinoneHCID 24497Calcium Sulfate

Product 1

HCID 11322818HCID 11322818, compoundYield 70%

Reagents, catalysts & solvents 3

HCID 244Benzyl AlcoholSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4 g of 2-acetyl hydroquinone (I) in 90 ml of ethyl acetate, 100 ml of acetonitrile and 5 ml of benzyl alcohol (III) are added 60 g of crushed calcium sulfate oven dried at 240° C., then 8.5 g of powdered cuprous chloride. It is agitated in gaseous oxygen (at a pressure of one atmosphere) for two hours and thirty minutes at ambient temperature. Then it is diluted with toluene, filtered, the filtrate is evaporated, the residue taken up in a mixture of 120 ml of ether and 80 ml of cyclohexane; by trituration of the resulting mixture followed by a filtration separation of the insoluble matter, a solution is obtained which leads to the expected compound (Yield≃70%) after evaporation of the solvents.

Workup

  1. customdried at 240° C.
  2. customthirty minutes
  3. customat ambient temperature
  4. additionThen it is diluted with toluene
  5. filtrationfiltered
  6. customthe filtrate is evaporated
  7. additionthe residue taken up in a mixture of 120 ml of ether and 80 ml of cyclohexane
  8. filtrationby trituration of the resulting mixture followed by a filtration separation of the insoluble matter
  9. customa solution is obtained which

Sources & evidence

ORD record
ord-c711257014814c93b7a67f207396f59f
Source dataset
uspto-grants-1984_12
Patent number
US04486349

Reaction notes

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