2-(prop-2-enoxymethyl)oxirane

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:55.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Into a 2.5 liter SUS separable flask equipped with a reflux condenser and a stirrer, 500.0 g of pure water, 399.3 g of iminodiacetic acid (IDA) and 500.0 g of a 48% aqueous solution of sodium hydroxide (hereinafter, abbreviated as 48% NaOH) were charged, and a temperature of the mixture was adjusted to 55° C. while stirring the mixture. Then, 342.4 g of allyl glycidyl ether (AGE) was slowly added dropwise to a reaction system maintained at 55° C. over two hours while stirring. On completion of adding dropwise, the reaction solution was further aged at 55° C. for 1 hour to produce a 50% aqueous solution of AGE-IDA (hereinafter, abbreviated as 50% AGE-IDA). Into a 2.5 liter SUS separable flask equipped with a reflux condenser and a stirrer were charged was adjusted to 55° C. while stirring On completion of adding dropwise

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1-(2-trimethylsilylethyl)-1,1,3,3-tetramethyldisiloxane (18.8 g) and chloroplatininc acid catalyst (ethanolic solution, 30 ppm Pt) were charged to a 100 ml round-bottomed (RB) flask equipped with a magnetic stirrer, reflux condenser, and N2 inlet. The mixture was stirred and heated to 90° C. 2-Allyloxymethyl-oxirane (10 g) was placed in an addition funnel and added dropwise to the flask. The mixture was stirred and maintained at 90° C. for an additional 4 hours. Reaction progress was followed by NMR spectroscopy. Upon reaction completion, excess 2-allyloxymethyl-oxirane was removed by vacuum distillation. equipped with a magnetic stirrer reflux condenser, and N2 inlet added dropwise to the flask The mixture was stirred maintained at 90° C. for an additional 4 hours Reaction progress was removed by vacuum distillation

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Using the method of Example 15, supra, allyl glycidyl ether (119 μL, 1.0 mmol) and 1,1-dimethyl-2-(4-methoxyphenyl)ethylamine (197 mg, 1.1 mmol) were used to prepare 79 mg of the title compound as a clear, colorless oil: GC/EI-MS, m/z (rel. int.) 294 (M+1, 0.1), 278 (0.9), 222 (1.5), 172 (100), 163 (11), 121 (20); 1H-NMR (CDCl3) δ 7.04 (2H, d, J=8.6), 6.79 (2H, d, J=8.6), 5.85 (1H, ddd, J=22.2, 10.5 and 5.7), 5.23 (1H, dd, J=17.3 and 1.5), 5.14 (1H, dd, J=10.3 and 1.5), 3.96 (2H, d, J=5.7), 3.74 (4H, m), 3.43 (2H, d, J=5.7), 2.83 (1H, broad s), 2.77 (1H, dd, J=11.7 and 4.1), 2.62 (5H, m), 1.02 (3H, s), 1.01 (3H, S); 13C-NMR (CDCl3) δ 158.0, 134.5, 131.3, 129.9, 117.0, 113.3, 72.8, 72.2, 69.0, 55.0, 53.3, 46.3, 44.5, 26.6, 26.4.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Copolymers of glycidyl propionate and allyl glycidyl ether and a copolymer of glycidyl butyrate and allyl glycidyl ether were prepared in the same way as in Example 4.