Glycidyl methacrylate → 3-(Methacryloyloxy)-2-hydroxypropyl bicyclo[2.2.1]hept-2-ene-6-carboxylate

HRID 325437

Reaction equation

HRID 325437 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(C1C(O)=C(C(C)(C)C)C=C(C)C=1)(C)(C)C.[CH:27]12[CH2:36][CH:30]([CH2:31][CH:32]1[C:33]([OH:35])=[O:34])[CH:29]=[CH:28]2>[Cl-].C[N+](C)(C)C>[CH:27]12[CH2:36][CH:30]([CH2:31][CH:32]1[C:33]([O:35][CH2:9][CH:8]([OH:10])[CH2:7][O:6][C:1](=[O:5])[C:2]([CH3:4])=[CH2:3])=[O:34])[CH:29]=[CH:28]2

Participants

5

Reactant 3

HCID 7837Glycidyl methacrylateHCID 314042,6-Di-tert-butyl-4-methylphenolHCID 789495-Norbornene-2-carboxylic acid

Product 1

HCID 204648873-(Methacryloyloxy)-2-hydroxypropyl bicyclo[2.2.1]hept-2-ene-6-carboxylate

Reagents, catalysts & solvents 1

HCID 6379Tetramethylammonium chlorideCatalyst

Conditions

Temperature
100 °C

Procedure

Glycidyl methacrylate (43 g), containing 0.13 g of 2,6-di-tert. butyl-p-cresol and 0.26 g of tetramethylammonium chloride, was heated to 100° C. and bicyclo[2.2.1]hept-2-ene-6-carboxylic acid (41.8 g) was added slowly over about 1 hour, so that the temperature of the mixture did not exceed 105° C. Heating at 100° C. was continued for a further three hours, by which time the epoxide content of the product was negligible. The above-mentioned ester was a colourless mobile liquid.

Workup

  1. customdid not exceed 105° C
  2. temperatureHeating at 100° C.

Sources & evidence

ORD record
ord-470fca31966c4896beb4e9655bb84390
Source dataset
uspto-grants-1984_04
Patent number
US04440850

Linked notes

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