Diethyl Ether → 1-Ethoxyethyl Methacrylate (stabilized with MEHQ)
Reaction equation
[C:1]([OH:6])(=[O:5])[C:2]([CH3:4])=[CH2:3].C(Cl)Cl.N1C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:27]([O:29][CH2:30][CH3:31])[CH3:28]>>[CH2:27]([O:29][CH:30]([O:5][C:1](=[O:6])[C:2]([CH3:4])=[CH2:3])[CH3:31])[CH3:28]Participants
Procedure
In a flask having four inlets, 15.1 grams (0.21 mols) of ethylvinylehter and 20 grams (0.23 mols) of methacrylic acid were dissolved into 200 ml of methylene chloride. Then, 0.53 grams (0.0021 mols) of p-toluenesulfonic acid pyridine salt was added to the mixture, and stirred for complete dissolution of p-toluenesulfonic acid pyridine salt into the mixture. The resultant solution was stood at room temperature for six hours. Then, 200 ml of diethylether was added into the solution. The resultant solution was washed three times with 2.5% aqueous sodium hydroxide, and further six times with water. Then, an ether layer was dehydrated with magnesium sulfate. After filtering magnesium sulfate out, a methylene chloride layer was evaporated. As a result, there was obtained 31.8 grams of 1-ethoxyethylmethacrylate. The yield was 96%. With respect to a structure of the target material, IR was measured with an analyzer, IR-470 model available from Shimazu Seisakusho, and 1H-NMR was measured with an analyzer, AMX-400 model available from Bruker Instruments.
Workup
- customIn a flask having
- washThe resultant solution was washed three times with 2.5% aqueous sodium hydroxide, and further six times with water
- filtrationAfter filtering magnesium sulfate out
- customa methylene chloride layer was evaporated
Sources & evidence
- ORD record
- ord-7084982bea3a48adae3254909bc11379
- Source dataset
- uspto-grants-1999_11
- Patent number
- US05994025
Reaction notes
Loading…