Reaction #833531

Reaction equation

1-chloromethyl-2-methyl-2-propanol

sodium methacrylate

phenothiazine

→

2-hydroxy-2,2-dimethylethyl methacrylate

Solvents

hexane

butyronitrile

Conditions

Workup

1. 1
   Temperaturewas heated
2. 2
   Temperatureto reflux under nitrogen in a three-necked round bottomed flask
3. 3
   Otherequipped with a condenser and a mechanical stirrer
4. 4
   Filtrationfiltered through celite
5. 5
   OtherThe solvents were removed under aspirator vacuum (40-80° C.)
6. 6
   workup.DISTILLATIONThe residue was distilled under high vacuum
7. 7
   OtherThe 22.50 grams of the product was collected between 72-80° C. at 2 mm pressure as a clear liquid

Procedure

A mixture of 1-chloromethyl-2-methyl-2-propanol (21.80 g, 0.20 mole), sodium methacrylate (32.40 g, 0.30 mole), Adogen 464 (7.00 g, 0.015 mole) (phase transfer catalyst purchased from Aldrich Chemical Co.), and phenothiazine (60 mg) in butyronitrile (200 ml) was heated to reflux under nitrogen in a three-necked round bottomed flask equipped with a condenser and a mechanical stirrer. After cooling the contents to room temperature, the mixture was diluted with hexane (200 ml) and filtered through celite. The solvents were removed under aspirator vacuum (40-80° C.). The residue was distilled under high vacuum. The 22.50 grams of the product was collected between 72-80° C. at 2 mm pressure as a clear liquid.

Source