Glycidyl methacrylate → 3-Ethoxy-4-hydroxymandelic acid

Participants

Reaction Conditions

Reaction Steps

A 250 ml round bottom flask, equipped with a mechanical stirrer, thermometer, and nitrogen inlet, is charged with tetrahydrofuran THF (75.6 gm), 1-trimethylsiloxy-1-methoxy-2-methylpropene (7.0 gm, 0.0402M), xylene (1.0 gm), and tetrabutylammonium m-chlorobenzoate (400 μl of a 1.0M solution in acetonitrile). The flask is cooled to 10° C. Feed I consists of tetrahydrofuran (4.0 gm) and tetrabutylammonium m-chlorobenzoate (400 μl of a 1.0M solution). It is added over 50 minutes. Feed II is glycidyl methacrylate (17.3 gm, 0.122M). It is started simultaneously with the start of the feed I. Feed II is added over one minute. Feed III is 2-ethylhexyl methacrylate (40.7 gm, 0.206M). Feed III is started 9 minutes after feed I has begun. Feed III is added over 30 minutes. The temperature of the flask rises to about 41.0° C. After feed I is completed the flask is cooled to 10° C. Feed IV is glycidyl methacrylate (17.1 gm, 0.120M). It is started 8 minutes after feed I is completed. Feed IV is added over 1 minute. At 70 minutes of total reaction time (11 minutes after feed IV is completed) methanol (10.0 gm) is added to the flask.

Provenance & Evidence