Hydroquinone → HCID 12570756, compound

HRID 1701662Notes

Reaction equation

HRID 1701662 reaction equation
[CH3:1][Si:2]1([CH3:8])[CH2:7][CH2:6][CH2:5][CH2:4][O:3]1.[C:9]([OH:13])(=[O:12])[CH:10]=[CH2:11].[C:14]1([CH:21]=[CH:20][C:18]([OH:19])=CC=1)O.S(=O)(=O)(O)O>C1CCCCC1>[C:9]([O:13][CH2:4][CH2:5][CH2:6][CH2:7][Si:2]([CH3:8])([CH3:1])[O:3][Si:2]([CH3:7])([CH3:1])[CH2:14][CH2:21][CH2:20][CH2:18][O:19][C:4](=[O:3])[CH:5]=[CH2:6])(=[O:12])[CH:10]=[CH2:11]

Participants

6

Reactant 4

HCID 785HydroquinoneHCID 1118Sulfuric AcidHCID 6581Acrylic AcidHCID 799091-Oxa-2-silacyclohexane, 2,2-dimethyl-

Product 1

HCID 12570756HCID 12570756, compound

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Conditions

Temperature
100 °C

Procedure

523.8 g. 1,1-dimethyl-1-sila-2-oxacyclohexane (4.0 moles), 304.7 g. acrylic acid (4.2 moles), 1.0 g. hydroquinone, 13.5 ml concentrated sulfuric acid, and 1200 ml cyclohexane are measured into a 3 liter reactor. The mixture is stirred during heating. The mixture is heated with steam (100° C.) and kept under dry air. Water formed during the reaction is removed continuously as the cyclohexane and water azeotrope. After 6 hrs. of heating, 31.9 ml water is collected and heating is stopped. The solution is then column filtered over 1 kg. activated alumina and filtered again over 740 g. grade 12 silica gel. The cyclohexane is removed from the product by rotary evaporation at reduced pressure. 1,3-bis (4-acryloxy butyl) tetramethyl disiloxane is obtained. The product is 98.3% pure by gas chromatography. The identity of the product is confirmed by infrared spectrum and elemental analysis. The analysis results are 55.96% C, 9.26% H, and 13.85% Si.

Workup

  1. temperatureduring heating
  2. customunder dry air
  3. customWater formed during the reaction
  4. customis removed continuously as the cyclohexane and water
  5. temperatureof heating
  6. custom31.9 ml water is collected
  7. temperatureheating
  8. filtrationcolumn filtered over 1 kg
  9. filtrationfiltered again over 740 g
  10. customThe cyclohexane is removed from the product by rotary evaporation at reduced pressure

Sources & evidence

ORD record
ord-1c2b800b7ac64685aed2f0ffcc36b76a
Source dataset
uspto-grants-1980_03
Patent number
US04195030

Reaction notes

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