Reaction #312577

ord-65df79f8fb1645f5a42c2fdef4c0b081

Reaction equation

C=C(C)C(=O)OCC(=O)O
Hydroxycarbonylmethyl methacrylate
OC1C2CC3CC(C2)CC1(O)C3
dihydroxyadamantane
Cc1ccc(S(=O)(=O)O)cc1
p-toluenesulfonic acid
→
C=C(C)C(=O)OCC(=O)OC12CC3CC(CC(O)(C3)C1)C2
oil
C=C(C)C(=O)OCC(=O)OC12CC3CC(CC(O)(C3)C1)C2
(3-hydroxyadamantyloxycarbonyl)methyl methacrylate

Reactants

C=C(C)C(=O)OCC(=O)O
Hydroxycarbonylmethyl methacrylate
OC1C2CC3CC(C2)CC1(O)C3
dihydroxyadamantane
Cc1ccc(S(=O)(=O)O)cc1
p-toluenesulfonic acid

Reagents

None

Solvents

ClCCl
dichloromethane

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    workup.ADDITIONwas added
  2. 2
    TemperatureThen, the mixture was refluxed for 15 hours
  3. 3
    Otherwhile removing water
  4. 4
    OtherAfter the reaction

Procedure

Hydroxycarbonylmethyl methacrylate (30 g) and dihydroxyadamantane (16.8) were added into dichloromethane (500 ml), and p-toluenesulfonic acid (1 g) was added thereto. Then, the mixture was refluxed for 15 hours while removing water generated. After the reaction, conventional after-treatments were carried out to obtain oil (21.2 g), which was identified to be Monomer A described above.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07556908B2uspto-grants-2009_07