Hydroquinone → HCID 118117372, compound

Temperature

72.5 °C

A round-bottom flask equipped with a stirring bar, a reflux condenser and a dropping funnel was charged with 1.6 g of 4-vinyl-1-cyclohexene 1,2-epoxide, and was heated to 70-75° C. At this point catalytic amount of platinum(0)-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex solution in xylene, (Pt around 2%) was added and the reaction mixture was further heated to 90° C. To this reaction mixture, 10 g of monohydride functionalized polydimethylsiloxane, was added drop-wise. After completion of reaction, the reaction mixture was cooled down to 70-75° C. and 20 mL of Toluene, and a catalytic amount of Titanium isopropoxide and TEMPO (2,2,6,6-Tetramethylpiperidine 1-oxyl) was added and the reaction mixture was further heated to 90-95° C. To this reaction mixture, 1.7 g of acrylic acid, was added drop-wise over a period of two hours. The reaction was monitored using 1H-NMR spectroscopy. After completion of reaction, the reaction mixture was cooled down again to 75° C. and 2.5 g of succinic anhydride, 2.5 g of triethylamine, and 300 ppm of hydroquinone was added. The reaction was monitored using 1H-NMR spectroscopy. After completion the product was vacuum striped, re-dissolved in dichloromethane and washed with hot brine solution. The organic phase was passed over Tulsion T66-MP resin to remove traces of triethylamine and decolorized using activated charcoal. The organic layer was filtered over Celite column to remove charcoal and then stirred along with Dowex WBA resin to remove traces of acrylic acid. The organic phase was further filtered and concentrated to yield pale yellow color viscous product.

1. customA round-bottom flask equipped with a stirring bar, a reflux condenser and a dropping funnel
2. temperaturethe reaction mixture was further heated to 90° C
3. customAfter completion of reaction
4. temperaturethe reaction mixture was cooled down to 70-75° C.
5. temperaturethe reaction mixture was further heated to 90-95° C
6. customAfter completion of reaction
7. temperaturethe reaction mixture was cooled down again to 75° C.
8. washwashed with hot brine solution
9. customto remove traces of triethylamine
10. filtrationThe organic layer was filtered over Celite column
11. customto remove charcoal
12. customto remove traces of acrylic acid
13. filtrationThe organic phase was further filtered
14. concentrationconcentrated
15. customto yield pale yellow color viscous product

ORD record

ord-a7048d3bbfa14efa84ad26e2922eac4e

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09296764B2