2-(2-chloroacetyl)oxyethyl 2-chloroacetate

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

Procedure: In a 2 liter, 4 necked round bottom flask equipped with a mechanical stirrer, a solution of ethylene glycol (100 grams, 1.611 moles), chloroacetic acid (385 grams, 4.031 moles) and para toluenesulphonic acid (1 gram) in toluene (750 ml), was refluxed for 8 hours using a Dean-Stark apparatus. It was then cooled to room temperature. The toluene layer was washed with water (2×300 ml), 5% sodium bicarbonate solution (3×500 ml) and again with water (2×300 ml), dried over sodium sulfate, and distilled to provide crude 1, which was purified by high vacuum distillation to provide pure 1 (242 grams, 69.8%), which slowly crystallized to white crystals. m.p: 44° C., 1H NMR (CDCl3) δ 4.16 (s, 2H, CH2), 4.85 (s, 2H, CH2) In a 2 liter, 4 necked round bottom flask equipped with a mechanical stirrer The toluene layer was washed with water (2×300 ml), 5% sodium bicarbonate solution (3×500 ml) and again with water (2×300 ml) dried over sodium sulfate distilled to provide crude 1, which was purified by high vacuum distillation

Conditions: temp:150.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Ethylene bis[(diethyl phosphono)acetate] was prepared by a modification of the procedure described in U.S. Pat. No. 3,943,200 employing a shorter reaction time and lower final temperature. To ethylene bis(chloroacetate) (107.5 g, 0.5 mol) under nitrogen at 150° C. triethyl phosphite (166.0 g, 1.0 mol) was slowly added over 60 minutes with stirring, and the reaction mixture was maintained at 150° C. for a further 3 hours. Continuous evolution of ethyl chloride occurred throughout the reaction. Removal of volatiles under vacuum gave ethylene bis [(diethyl phosphono) acetates as a straw-coloured liquid (197.5 g, 95%), identified by NMR. 3,943,200 employing a shorter reaction time Removal of volatiles under vacuum

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

Procedure: In a 2 liter, 4 necked round bottom flask equipped with a mechanical stirrer, a solution of ethylene glycol (100 grams, 1.611 moles), chloroacetic acid (385 grams, 4.031 moles) and para toluenesulphonic acid (1 gram) in toluene (750 ml), was refluxed for 8 hours using a Dean-Stark apparatus. It was then cooled to room temperature. The toluene layer was washed with water (2×300 ml), 5% sodium bicarbonate solution (3×500 ml) and again with water (2×300 ml), dried over sodium sulfate, and distilled to provide crude 1, which was purified by high vacuum distillation to provide pure 1 (242 grams, 69.8%), which slowly crystallized to white crystals. m.p: 44° C., IH NMR (CDCl3) δ4.16 (s, 2H, CH2), 4.85 (s, 2H, CH2) In a 2 liter, 4 necked round bottom flask equipped with a mechanical stirrer The toluene layer was washed with water (2×300 ml), 5% sodium bicarbonate solution (3×500 ml) and again with water (2×300 ml) dried over sodium sulfate distilled to provide crude 1, which was purified by high vacuum distillation

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

Procedure: In a 2 liter, 4 necked round bottom flask equipped with a mechanical stirrer, a solution of ethylene glycol (100 grams, 1.611 moles), chloroacetic acid (385 grams, 4.031 moles) and para toluenesulphonic acid (1 gram) in toluene (750 ml), was refluxed for 8 hours using a Dean-Stark apparatus. It was then cooled to room temperature. The toluene layer was washed with water (2×300 ml), 5% sodium bicarbonate solution (3×500 ml) and again with water (2×300 ml), dried over sodium sulfate, and distilled to provide crude 1, which was purified by high vacuum distillation to provide pure 1 (242 grams, 69.8%), which slowly crystallized to white crystals. m.p: 44° C., IH NMR (CDCl3) δ4.16 (s, 2H, CH2), 4.85 (s, 2H, CH2) In a 2 liter, 4 necked round bottom flask equipped with a mechanical stirrer The toluene layer was washed with water (2×300 ml), 5% sodium bicarbonate solution (3×500 ml) and again with water (2×300 ml) dried over sodium sulfate distilled to provide crude 1, which was purified by high vacuum distillation

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

Procedure: In a 2 liter, 4 necked round bottom flask equipped with a mechanical stirrer, a solution of ethylene glycol (100 grams, 1.611 moles), chloroacetic acid (385 grams, 4.031 moles) and para toluenesulphonic acid (1 gram) in toluene (750 ml), was refluxed for 8 hours using a Dean-Stark apparatus. It was then cooled to room temperature. The toluene layer was washed with water (2×300 ml), 5% sodium bicarbonate solution (3×500 ml) and again with water (2×300 ml), dried over sodium sulfate, and distilled to provide crude 1, which was purified by high vacuum distillation to provide pure 1 (242 grams, 69.8%), which slowly crystallized to white crystals. m.p: 44° C., 1H NMR (CDCl3) δ 4.16 (s, 2H, CH2), 4.85 (s, 2H, CH2) In a 2 liter, 4 necked round bottom flask equipped with a mechanical stirrer The toluene layer was washed with water (2×300 ml), 5% sodium bicarbonate solution (3×500 ml) and again with water (2×300 ml) dried over sodium sulfate distilled to provide crude 1, which was purified by high vacuum distillation

Conditions: temp:150.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Ethylene bis[(diethyl phosphono)acetate] was prepared by a modification of the procedure described in U.S. Pat. No. 3,943,200 employing a shorter reaction time and lower final temperature. To ethylene bis(chloroacetate) (107.5 g, 0.5 mol) under nitrogen at 150° C. triethyl phosphite (166.0 g, 1.0 mol) was slowly added over 60 minutes with stirring, and the reaction mixture was maintained at 150° C. for a further 3 hours. Continuous evolution of ethyl chloride occurred throughout the reaction. Removal of volatiles under vacuum gave ethylene bis [(diethyl phosphono) acetates as a straw-coloured liquid (197.5 g, 95%), identified by NMR. 3,943,200 employing a shorter reaction time Removal of volatiles under vacuum

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

Procedure: In a 2 liter, 4 necked round bottom flask equipped with a mechanical stirrer, a solution of ethylene glycol (100 grams, 1.611 moles), chloroacetic acid (385 grams, 4.031 moles) and para toluenesulphonic acid (1 gram) in toluene (750 ml), was refluxed for 8 hours using a Dean-Stark apparatus. It was then cooled to room temperature. The toluene layer was washed with water (2×300 ml), 5% sodium bicarbonate solution (3×500 ml) and again with water (2×300 ml), dried over sodium sulfate, and distilled to provide crude 1, which was purified by high vacuum distillation to provide pure 1 (242 grams, 69.8%), which slowly crystallized to white crystals. m.p: 44° C., IH NMR (CDCl3) δ4.16 (s, 2H, CH2), 4.85 (s, 2H, CH2) In a 2 liter, 4 necked round bottom flask equipped with a mechanical stirrer The toluene layer was washed with water (2×300 ml), 5% sodium bicarbonate solution (3×500 ml) and again with water (2×300 ml) dried over sodium sulfate distilled to provide crude 1, which was purified by high vacuum distillation

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

Procedure: In a 2 liter, 4 necked round bottom flask equipped with a mechanical stirrer, a solution of ethylene glycol (100 grams, 1.611 moles), chloroacetic acid (385 grams, 4.031 moles) and para toluenesulphonic acid (1 gram) in toluene (750 ml), was refluxed for 8 hours using a Dean-Stark apparatus. It was then cooled to room temperature. The toluene layer was washed with water (2×300 ml), 5% sodium bicarbonate solution (3×500 ml) and again with water (2×300 ml), dried over sodium sulfate, and distilled to provide crude 1, which was purified by high vacuum distillation to provide pure 1 (242 grams, 69.8%), which slowly crystallized to white crystals. m.p: 44° C., 1H NMR (CDCl3) δ 4.16 (s, 2H, CH2), 4.85 (s, 2H, CH2) In a 2 liter, 4 necked round bottom flask equipped with a mechanical stirrer The toluene layer was washed with water (2×300 ml), 5% sodium bicarbonate solution (3×500 ml) and again with water (2×300 ml) dried over sodium sulfate distilled to provide crude 1, which was purified by high vacuum distillation