Glycidyl methacrylate → 3-(Methacryloyloxy)-2-hydroxypropyl methyl-5-carbomethoxybicyclo-[2.2.1]hept-2-ene-6-carboxylate

HRID 325438

Reaction equation

HRID 325438 reaction equation
[CH3:1][C:2]12[CH2:15][CH:5]([CH:6]([C:11]([O:13][CH3:14])=[O:12])[CH:7]1[C:8]([OH:10])=[O:9])[CH:4]=[CH:3]2.[C:16]([O:21][CH2:22][CH:23]1[O:25][CH2:24]1)(=[O:20])[C:17]([CH3:19])=[CH2:18].C(C1C(O)=C(C(C)(C)C)C=C(C)C=1)(C)(C)C>[Cl-].C[N+](C)(C)C>[CH3:1][C:2]12[CH2:15][CH:5]([CH:6]([C:11]([O:13][CH3:14])=[O:12])[CH:7]1[C:8]([O:10][CH2:24][CH:23]([OH:25])[CH2:22][O:21][C:16](=[O:20])[C:17]([CH3:19])=[CH2:18])=[O:9])[CH:4]=[CH:3]2

Participants

5

Reactant 3

HCID 7837Glycidyl methacrylateHCID 314042,6-Di-tert-butyl-4-methylphenolHCID 54301392Methyl-5-carbomethoxybicyclo [2.2.1]hept-2-ene-6-carboxylic acid

Product 1

HCID 204648893-(Methacryloyloxy)-2-hydroxypropyl methyl-5-carbomethoxybicyclo-[2.2.1]hept-2-ene-6-carboxylate

Reagents, catalysts & solvents 1

HCID 6379Tetramethylammonium chlorideCatalyst

Procedure

This acid ester (50 g) was heated with glycidyl methacrylate (40 g) at 100° C. in the presence of 0.27 g of tetramethylammonium chloride and 0.13 g of 2,6-di-tert.butyl-p-cresol until the epoxide content had fallen to a negligible level; the desired ester so formed was a viscous liquid.

Sources & evidence

ORD record
ord-5a7f171be5fc4b768eb0eb9d95b8dd57
Source dataset
uspto-grants-1984_04
Patent number
US04440850

Linked notes

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