Hydroquinone → DIVINYL SEBACATE

HRID 1464858Notes

Reaction equation

HRID 1464858 reaction equation
[C:1]([OH:14])(=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([OH:12])=[O:11].[C:15]1(C=CC(O)=C[CH:17]=1)O.[C:23]1(C)C=CC(S(O)(=O)=O)=C[CH:24]=1>C(OC=C)(=O)C.C(OCC)(=O)C.C([O-])(=O)C.[Hg+2].C([O-])(=O)C>[CH:15]([O:11][C:10](=[O:12])[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][C:1]([O:14][CH:23]=[CH2:24])=[O:13])=[CH2:17]

Participants

7

Reactant 3

HCID 785HydroquinoneHCID 5192Sebacic AcidHCID 6101p-Toluenesulfonic acid

Product 1

HCID 11414135DIVINYL SEBACATE

Reagents, catalysts & solvents 3

HCID 15337Mercuric acetateCatalystHCID 7904Vinyl AcetateSolventHCID 8857Ethyl AcetateSolvent

Procedure

15 g (74.2 mmol) of sebacic acid, 0.66 g (2.06 mmol) of mercury(II)acetate, and 0.12 g of hydroquinone were precharged in 75 ml of vinyl acetate into a 250 ml three-necked flask and stirred for 20 minutes under argon. Then, 0.09 g (0.01 mol) of p-toluenesulfonic acid were added as a catalyst, and the reaction mixture was refluxed for 4 hours. After cooling down to room temperature, the obtained solution was diluted with 200 ml ethyl acetate and extracted with 150 ml 2N NaOH. The organic phase was dried over Na2SO4, and the volatile components were removed on a rotary evaporator. Purification by flash column chromatography on silica gel (PE:EE=10:1) yielded 8.9 g (47% of th.) of a colorless liquid.

Workup

  1. temperaturethe reaction mixture was refluxed for 4 hours
  2. extractionextracted with 150 ml 2N NaOH
  3. dry with materialThe organic phase was dried over Na2SO4
  4. customthe volatile components were removed on a rotary evaporator
  5. customPurification by flash column chromatography on silica gel (PE:EE=10:1)
  6. customyielded 8.9 g (47% of th.) of a colorless liquid

Sources & evidence

ORD record
ord-ed1d01ef8e5e418a858c73634ac4968f
Source dataset
uspto-grants-2015_04
Patent number
US08999323B2

Reaction notes

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