Hydroquinone → HCID 131735170, compound

HRID 931403Notes

Reaction equation

HRID 931403 reaction equation
[C:1]([NH:6][CH2:7][C:8]([O:10][CH:11]1[CH2:16][CH2:15][CH:14]([CH2:17][CH2:18][Si:19]([CH3:30])([O:25][Si:26]([CH3:29])([CH3:28])[CH3:27])[O:20][Si:21]([CH3:24])([CH3:23])[CH3:22])[CH2:13][CH:12]1[OH:31])=[O:9])(=[O:5])[C:2]([CH3:4])=[CH2:3].C1(C)C=CC=CC=1.[C:39]1(=[O:45])[O:44][C:42](=[O:43])[CH2:41][CH2:40]1.C1(C=CC(O)=CC=1)O>C(Cl)(Cl)Cl.C(N(CC)CC)C>[CH3:29][Si:26]([CH3:27])([CH3:28])[O:25][Si:19]([CH2:18][CH2:17][CH:14]1[CH2:13][CH:12]([O:31][C:39](=[O:45])[CH2:40][CH2:41][C:42]([OH:44])=[O:43])[CH:11]([O:10][C:8](=[O:9])[CH2:7][NH:6][C:1](=[O:5])[C:2]([CH3:4])=[CH2:3])[CH2:16][CH2:15]1)([CH3:30])[O:20][Si:21]([CH3:24])([CH3:23])[CH3:22]

Participants

7

Reactant 4

HCID 785HydroquinoneHCID 1140TolueneHCID 7922Succinic anhydrideHCID 131735171HCID 131735171, compound

Product 1

HCID 131735170HCID 131735170, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
62.5 °C

Procedure

15 g of 4-(2-(1,1,1,3,5,5,5-heptamethyltrisiloxan-3-yl)ethyl)-2-hydroxycyclohexyl 2-methacrylamidoacetate and 4.6 g of toluene and succinic anhydride are further charged into a round bottom flask equipped with a stirring bar, a reflux condenser, and nitrogen inlet. To this, triethylamine and hydroquinone are added as a catalyst and radical scavenger, respectively, and the reaction mixture is heated to 60-65° C. After completion, the product was vacuum striped, re-dissolved in chloroform, and washed with 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 concentrated after removal of the charcoal to yield a pale yellow, viscous product.

Workup

  1. customequipped with a stirring bar, a reflux condenser, and nitrogen inlet
  2. washwashed with brine solution
  3. customto remove traces of triethylamine
  4. concentrationThe organic layer was concentrated
  5. customafter removal of the charcoal
  6. customto yield a pale yellow, viscous product

Sources & evidence

ORD record
ord-81e6e45205e048e394541aafc9d7aeb9
Source dataset
uspto-grants-2016_03
Patent number
US09296764B2

Reaction notes

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