Methylhydroquinone → HCID 54543419, compound

HRID 1789188Notes

Reaction equation

HRID 1789188 reaction equation
[CH3:1][CH:2]([CH3:23])[CH2:3][CH:4]([O:6][Si:7]([O:16][CH:17]([CH2:19][CH:20]([CH3:22])[CH3:21])[CH3:18])([O:9][CH:10]([CH2:12][CH:13]([CH3:15])[CH3:14])[CH3:11])[OH:8])[CH3:5].C(N(CC)CC)C.[CH3:31][C:32]1C=C(O)C=C[C:33]=1[OH:34].C(Cl)(=O)C=C>C1(C)C=CC=CC=1>[C:33]([O:8][Si:7]([O:6][CH:4]([CH2:3][CH:2]([CH3:23])[CH3:1])[CH3:5])([O:16][CH:17]([CH2:19][CH:20]([CH3:22])[CH3:21])[CH3:18])[O:9][CH:10]([CH2:12][CH:13]([CH3:14])[CH3:15])[CH3:11])(=[O:34])[CH:32]=[CH2:31]

Participants

6

Reactant 4

HCID 7253MethylhydroquinoneHCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 20188875HCID 20188875, compound

Product 1

HCID 54543419HCID 54543419, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
5 °C

Procedure

0.23 moles of tris(4-methyl-2pentoxy)silanol, 0.23 moles of triethylamine, 0.02 gms. of methyl hydroquinone as polymerization inhibitor and 82 cc of toluene were placed in a three necked flask equipped with a stirrer, addition funnel, a thermometer and a condenser. A solution of 0.23 moles of acryloyl chloride in 23 cc of toluene was added slowly to the reaction mixture at 3°-5° C. At the end of the addition, the mass is allowed to stir for 1/2 hour at 5° C. The solid triethylamine hydrochloride was filtered and the solvent was distilled under vacuum. The residual crude product was distilled (bp 148°-162° C./3 mm/Hg) to give 41 gms. of product (G.C. purity 80%).

Workup

  1. customequipped with a stirrer, addition funnel
  2. additionAt the end of the addition
  3. filtrationThe solid triethylamine hydrochloride was filtered
  4. distillationthe solvent was distilled under vacuum
  5. distillationThe residual crude product was distilled (bp 148°-162° C./3 mm/Hg)
  6. customto give 41 gms

Sources & evidence

ORD record
ord-935ad146dc0f4ad9b7ad3ab45a8eb552
Source dataset
uspto-grants-1987_08
Patent number
US04687792

Reaction notes

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