Hydroquinone → HCID 131734266, compound

HRID 1500153Notes

Reaction equation

HRID 1500153 reaction equation
[C:1]([O:6][CH2:7][CH:8]1[O:10][CH2:9]1)(=[O:5])[C:2]([CH3:4])=[CH2:3].[C:11]1([CH:18]=[CH:17][C:15]([OH:16])=[CH:14][CH:13]=1)[OH:12]>C([O-])(=O)CCCCCC.[Cr+3].C([O-])(=O)CCCCCC.C([O-])(=O)CCCCCC.CC1C=CC=CC=1C>[C:1]([O:6][CH2:7][CH:8]1[O:10][CH2:9]1)(=[O:5])[C:2]([CH3:4])=[CH2:3].[C:11]1([CH:18]=[CH:17][C:15]([OH:16])=[CH:14][CH:13]=1)[OH:12]

Participants

5

Reactant 2

HCID 785HydroquinoneHCID 7837Glycidyl methacrylate

Product 1

HCID 131734266HCID 131734266, compound

Reagents, catalysts & solvents 2

HCID 173191Heptanoic acid, chromium(3+) salt (3:1)CatalystHCID 7237O-XyleneSolvent

Conditions

Temperature
142 °C

Procedure

A mixture of 9.95 g of glycidyl methacrylate, 4.40 g of hydroquinone, 0.050 g of HEPTCR 050 NPG (chromium heptanoate in polypropylene glycol) and 50 ml of o-xylene is initially charged in a 250 ml four-neck flask with a sabre stirrer (stirrer sleeve, stirrer motor), a thermometer, an inlet tube for compressed air, a reflux condenser and an oil bath with temperature regulation. The reaction mixture was heated to boiling with introduction of air. This was followed by refluxing at a reaction temperature (=internal flask temperature) of 142° C. for 10 h. After cooling to room temperature, the volatile constituents were removed in a rotary evaporator (bath temperature 55° C., vacuum 20 mbara). After filtration, a brown, cloudy liquid was obtained. The synthesis product was purified by means of column and thin-layer chromatography. The stationary phase used for column chromatography was silica gel 60 (0.063-0.200 mm); the eluent consisted of an ethyl acetate/cyclohexane mixture in a ratio of 1/1. The clear and colourless solutions obtained were combined to give three fractions. The eluent was subsequently removed on a rotary evaporator.

Workup

  1. additionis initially charged in a 250 ml four-neck flask with a sabre stirrer (stirrer sleeve, stirrer motor)
  2. temperatureThe reaction mixture was heated
  3. temperatureAfter cooling to room temperature
  4. customthe volatile constituents were removed in a rotary evaporator (bath temperature 55° C., vacuum 20 mbara)
  5. filtrationAfter filtration
  6. customa brown, cloudy liquid was obtained
  7. customThe synthesis product was purified by means of column and thin-layer chromatography
  8. customThe clear and colourless solutions obtained
  9. customto give three fractions
  10. customThe eluent was subsequently removed on a rotary evaporator

Sources & evidence

ORD record
ord-2386a8dfde05492fa3007e85f0673d24
Source dataset
uspto-grants-2015_12
Patent number
US09206112B2

Reaction notes

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