methyl (Z)-2-methylbut-2-enoate

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

Procedure: A mixture of 22.8 g. of methyl angelate, 10.0 g. of 3-methyl-4-pentenol, 100 ml. of toluene and 0.9 g. of dioctyltin laurate was reacted under the same conditions as in Example 1. The resulting mixture was subjected to single distillation to give 16.91 g. of a distillate boiling at 109° C. (21 mmHg). The distillate was further subjected to rectification to give 12.54 g. of a distillate boiling at 109° C. (21 mmHg). Analysis of the compound by gaschromatography done under the same conditions as in Example 12 indicated a purity of 99.653% in terms of the area ratio. Refractive index was 1.443. A mixture of 22.8 g The resulting mixture was subjected to single distillation to give 16.91 g to give 12.54 g

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

Procedure: A mixture of 22.8 g. of methyl angelate, 10 g. of 3-methyl-2-pentenol, 80 ml. of toluene and 1 g. of dioctyltin acetate was placed in a 300 ml. glass flask, which was equipped with a Soxhlet extractor filled on the top with molecular sieve 4A and a reflux cooler. The above mixture was heated under continuous reflux while returning the refluxed liquid through the molecular sieve 4A to the flask. The mixture resulted from the heating for a total of 17 hours was subjected to single distillation to give 14.2 g. of a distillate boiling at 115° C. (22 mmHg). The distillate was further subjected to rectification to give 9.70 g. of a distillate boiling at 115° C. (22 mmHg). Analysis of the compound by gaschromatography (Column: Silicone SE-52, 2%/chromosorb GHP) indicated a purity of 99.403% in terms of the area ratio. Refractive index (D ray, 20° C.) was 1.463. Infrared spectrum (liquid film) had absorptions at 2850-3020, 1720, 1670, 1650, 1455, 1385, 1350, 1255, 1225, 1155, 1080, 1040, 960, 845 and 760 cm-1. A mixture of 22.8 g glass flask, which was equipped with a Soxhlet extractor The above mixture was heated under continuous reflux The mixture resulted from the heating for a total of 17 hours was subjected to single distillation to give 14.2 g to give 9.70 g Refractive index (D ray, 20° C.)

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

Procedure: A mixture of 20.0 g. of methyl angelate, 26.34 g. of (Z)-3-hexenyl alcohol, 100 ml. of toluene and 1.2 g. of dioctyltin laurate was placed in a 300 ml. glass flask, which was equipped with a Soxhlet extractor filled on the top with molecular sieve 4A and a reflux cooler. A mixture of 20.0 g glass flask, which was equipped with a Soxhlet extractor

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

Procedure: A mixture of 20.0 g. of methyl angelate, 22.65 g. of 3-methyl-3-butenyl alcohol, 100 ml. of toluene and 0.8 g. of dioctyltin laurate was reacted under the same conditions as in Example 6. The reaction mixture was subjected to single distillation to obtain 39.5 g. of a distillate boiling at 104° C. (32 mmHg). A mixture of 20.0 g The reaction mixture was subjected to single distillation to obtain 39.5 g

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

Procedure: A mixture of 19.6 g. of methyl angelate, 22.2 g. of 3-methyl-2-butenyl alcohol, 100 ml. of toluene and 1.6 g. of dioctyltin laurate was placed in a glass flask which was equipped with a Soxhlet extractor filled with molecular sieve 4A on the top and a reflux cooler. The mixture was heated under reflux while returning the refluxed liquid through the molecular sieve 4A to the flask. The mixture obtained from the heating for a total of 26 hours was subjected to single distillation to give 24.24 g. of a distillate boiling at 102°-105° C. (25 mmHg). A mixture of 19.6 g which was equipped with a Soxhlet extractor The mixture was heated under reflux The mixture obtained from the heating for a total of 26 hours was subjected to single distillation to give 24.24 g

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

Procedure: A mixture of 22.8 g. of methyl angelate, 10.0 g. of 3-methyl-4-pentenol, 100 ml. of toluene and 0.9 g. of dioctyltin laurate was reacted under the same conditions as in Example 1. The resulting mixture was subjected to single distillation to give 16.91 g. of a distillate boiling at 109° C. (21 mmHg). The distillate was further subjected to rectification to give 12.54 g. of a distillate boiling at 109° C. (21 mmHg). Analysis of the compound by gaschromatography done under the same conditions as in Example 12 indicated a purity of 99.653% in terms of the area ratio. Refractive index was 1.443. A mixture of 22.8 g The resulting mixture was subjected to single distillation to give 16.91 g to give 12.54 g

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

Procedure: A mixture of 22.8 g. of methyl angelate, 10 g. of 3-methyl-2-pentenol, 80 ml. of toluene and 1 g. of dioctyltin acetate was placed in a 300 ml. glass flask, which was equipped with a Soxhlet extractor filled on the top with molecular sieve 4A and a reflux cooler. The above mixture was heated under continuous reflux while returning the refluxed liquid through the molecular sieve 4A to the flask. The mixture resulted from the heating for a total of 17 hours was subjected to single distillation to give 14.2 g. of a distillate boiling at 115° C. (22 mmHg). The distillate was further subjected to rectification to give 9.70 g. of a distillate boiling at 115° C. (22 mmHg). Analysis of the compound by gaschromatography (Column: Silicone SE-52, 2%/chromosorb GHP) indicated a purity of 99.403% in terms of the area ratio. Refractive index (D ray, 20° C.) was 1.463. Infrared spectrum (liquid film) had absorptions at 2850-3020, 1720, 1670, 1650, 1455, 1385, 1350, 1255, 1225, 1155, 1080, 1040, 960, 845 and 760 cm-1. A mixture of 22.8 g glass flask, which was equipped with a Soxhlet extractor The above mixture was heated under continuous reflux The mixture resulted from the heating for a total of 17 hours was subjected to single distillation to give 14.2 g to give 9.70 g Refractive index (D ray, 20° C.)

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

Procedure: A mixture of 20.0 g. of methyl angelate, 26.34 g. of (Z)-3-hexenyl alcohol, 100 ml. of toluene and 1.2 g. of dioctyltin laurate was placed in a 300 ml. glass flask, which was equipped with a Soxhlet extractor filled on the top with molecular sieve 4A and a reflux cooler. A mixture of 20.0 g glass flask, which was equipped with a Soxhlet extractor

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

Procedure: A mixture of 20.0 g. of methyl angelate, 22.65 g. of 3-methyl-3-butenyl alcohol, 100 ml. of toluene and 0.8 g. of dioctyltin laurate was reacted under the same conditions as in Example 6. The reaction mixture was subjected to single distillation to obtain 39.5 g. of a distillate boiling at 104° C. (32 mmHg). A mixture of 20.0 g The reaction mixture was subjected to single distillation to obtain 39.5 g

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

Procedure: A mixture of 19.6 g. of methyl angelate, 22.2 g. of 3-methyl-2-butenyl alcohol, 100 ml. of toluene and 1.6 g. of dioctyltin laurate was placed in a glass flask which was equipped with a Soxhlet extractor filled with molecular sieve 4A on the top and a reflux cooler. The mixture was heated under reflux while returning the refluxed liquid through the molecular sieve 4A to the flask. The mixture obtained from the heating for a total of 26 hours was subjected to single distillation to give 24.24 g. of a distillate boiling at 102°-105° C. (25 mmHg). A mixture of 19.6 g which was equipped with a Soxhlet extractor The mixture was heated under reflux The mixture obtained from the heating for a total of 26 hours was subjected to single distillation to give 24.24 g

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

Procedure: A mixture of 22.8 g. of methyl angelate, 10.0 g. of 3-methyl-4-pentenol, 100 ml. of toluene and 0.9 g. of dioctyltin laurate was reacted under the same conditions as in Example 1. The resulting mixture was subjected to single distillation to give 16.91 g. of a distillate boiling at 109° C. (21 mmHg). The distillate was further subjected to rectification to give 12.54 g. of a distillate boiling at 109° C. (21 mmHg). Analysis of the compound by gaschromatography done under the same conditions as in Example 12 indicated a purity of 99.653% in terms of the area ratio. Refractive index was 1.443. A mixture of 22.8 g The resulting mixture was subjected to single distillation to give 16.91 g to give 12.54 g

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

Procedure: A mixture of 22.8 g. of methyl angelate, 10 g. of 3-methyl-2-pentenol, 80 ml. of toluene and 1 g. of dioctyltin acetate was placed in a 300 ml. glass flask, which was equipped with a Soxhlet extractor filled on the top with molecular sieve 4A and a reflux cooler. The above mixture was heated under continuous reflux while returning the refluxed liquid through the molecular sieve 4A to the flask. The mixture resulted from the heating for a total of 17 hours was subjected to single distillation to give 14.2 g. of a distillate boiling at 115° C. (22 mmHg). The distillate was further subjected to rectification to give 9.70 g. of a distillate boiling at 115° C. (22 mmHg). Analysis of the compound by gaschromatography (Column: Silicone SE-52, 2%/chromosorb GHP) indicated a purity of 99.403% in terms of the area ratio. Refractive index (D ray, 20° C.) was 1.463. Infrared spectrum (liquid film) had absorptions at 2850-3020, 1720, 1670, 1650, 1455, 1385, 1350, 1255, 1225, 1155, 1080, 1040, 960, 845 and 760 cm-1. A mixture of 22.8 g glass flask, which was equipped with a Soxhlet extractor The above mixture was heated under continuous reflux The mixture resulted from the heating for a total of 17 hours was subjected to single distillation to give 14.2 g to give 9.70 g Refractive index (D ray, 20° C.)