[6-(hydroxymethyl)cyclohex-3-en-1-yl]methanol

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

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

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

Procedure: 4,5-di(hydroxymethyl)cyclohexene was epoxidized with m-chloroperbenzoic acid and thereby yielded 4,5-di(hydroxymethyl)cyclohexene oxide (cis-trans mixture). A mixture (280 mL) of sodium carbonate 24.9 g (0.23 mol) and toluene was heated to 95° C., and 1.4 g of propionic acid was added to the mixture. Maintaining the temperature of the reaction mixture, the mixture was combined with 19 g of vinyl acetate added dropwise, and fifteen minutes later, further combined with 1.27 g (1.9 mmol) of di-μ-chlorobis(1,5-cyclooctadiene)diiridium(I) [Ir(cod)Cl]2. Next, 30 g (0.19 mol) of 4,5-di(hydroxymethyl)cyclohexene oxide (cis-trans mixture) was added dropwise for three hours, and a reaction was carried out in a nitrogen atmosphere while adding dropwise 62 g of vinyl acetate and holding the reaction temperature at 95° C. After the completion of dropwise addition, the mixture was stirred for one hour. As the result of gas chromatography analysis of the mixture, it is confirmed that there were produced 4,5-di(vinyloxymethyl)cyclohexene oxide (cis-trans mixture) represented by following Formula (12) in a yield of 82% and 4-vinyloxymethyl-5-hydroxymethyl cyclohexene oxide (cis-trans mixture) in a yield of 4%. Purification of the reaction mixture by distillation yielded 31 g of 4,5-di-(vinyloxymethyl)cyclohexene oxide (cis-trans mixture) with a purity of 98%. Maintaining the temperature of the reaction mixture added dropwise fifteen minutes at 95° C After the completion of dropwise addition As the result of gas chromatography analysis of the mixture, it

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

Procedure: 4,5-di(hydroxymethyl)cyclohexene was epoxidized with m-chloroperbenzoic acid and thereby yielded 4,5-di(hydroxymethyl)cyclohexene oxide (cis-trans mixture). A mixture (280 mL) of sodium carbonate 24.9 g (0.23 mol) and toluene was heated to 95° C., and 1.4 g of propionic acid was added to the mixture. Maintaining the temperature of the reaction mixture, the mixture was combined with 19 g of vinyl acetate added dropwise, and fifteen minutes later, further combined with 1.27 g (1.9 mmol) of di-μ-chlorobis(1,5-cyclooctadiene)diiridium(I) [Ir(cod)Cl]2. Next, 30 g (0.19 mol) of 4,5-di(hydroxymethyl)cyclohexene oxide (cis-trans mixture) was added dropwise for three hours, and a reaction was carried out in a nitrogen atmosphere while adding dropwise 62 g of vinyl acetate and holding the reaction temperature at 95° C. After the completion of dropwise addition, the mixture was stirred for one hour. As the result of gas chromatography analysis of the mixture, it is confirmed that there were produced 4,5-di(vinyloxymethyl)cyclohexene oxide (cis-trans mixture) represented by following Formula (12) in a yield of 82% and 4-vinyloxymethyl-5-hydroxymethyl cyclohexene oxide (cis-trans mixture) in a yield of 4%. Purification of the reaction mixture by distillation yielded 31 g of 4,5-di-(vinyloxymethyl)cyclohexene oxide (cis-trans mixture) with a purity of 98%. Maintaining the temperature of the reaction mixture added dropwise fifteen minutes at 95° C After the completion of dropwise addition As the result of gas chromatography analysis of the mixture, it

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

Procedure: 30 g cis-1,2,3,6-tetrahydrophtalic acid anhydride in 150 ml abs. THF are added through a separating funnel to a solution of 45 g lithium aluminum hydride in 900 ml abs. THF and heated for 48 hours under reflux. Then the mixture is first cooled to room temperature and then in an ice-brine bath to about 15° C. and the unused portion of the hydride is carefully broken down with water. Through the addition of diluted sulphuric acid the salts are dissolved and through the addition of diethylether the organic phase is separated from the aqueous phase. under reflux is separated from the aqueous phase

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

Procedure: A solution of one hundred (100) parts by weight of a 1,2,3,6-tetrahydrophthalic anhydride in 500 parts of dry tetrahydrofuran is slowly added to a stirring mixture of 28.75 parts of lithium aluminum hydride and 162 parts of tetrahydrofuran. After the addition is complete, the mixture is refluxed for 24 hours. It is then hydrolyzed by a slow addition of a saturated Rochelle salt solution until it turns white. The mixture is refluxed for an additional 10 hours, allowed to room temperature, and suction filtered. The solvent is removed by a distillation and the viscous liquid crude product is purified by a fractional distillation under vacuum (yield 82%. b.p.: 165-170° C. at 12 mm). After the addition the mixture is refluxed for 24 hours The mixture is refluxed for an additional 10 hours allowed to room temperature suction filtered The solvent is removed by a distillation the viscous liquid crude product is purified by a fractional distillation under vacuum (yield 82%. b.p.: 165-170° C. at 12 mm)

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

Procedure: 4,5-di(hydroxymethyl)cyclohexene was epoxidized with m-chloroperbenzoic acid and thereby yielded 4,5-di(hydroxymethyl)cyclohexene oxide (cis-trans mixture). A mixture (280 mL) of sodium carbonate 24.9 g (0.23 mol) and toluene was heated to 95° C., and 1.4 g of propionic acid was added to the mixture. Maintaining the temperature of the reaction mixture, the mixture was combined with 19 g of vinyl acetate added dropwise, and fifteen minutes later, further combined with 1.27 g (1.9 mmol) of di-μ-chlorobis(1,5-cyclooctadiene)diiridium(I) [Ir(cod)Cl]2. Next, 30 g (0.19 mol) of 4,5-di(hydroxymethyl)cyclohexene oxide (cis-trans mixture) was added dropwise for three hours, and a reaction was carried out in a nitrogen atmosphere while adding dropwise 62 g of vinyl acetate and holding the reaction temperature at 95° C. After the completion of dropwise addition, the mixture was stirred for one hour. As the result of gas chromatography analysis of the mixture, it is confirmed that there were produced 4,5-di(vinyloxymethyl)cyclohexene oxide (cis-trans mixture) represented by following Formula (12) in a yield of 82% and 4-vinyloxymethyl-5-hydroxymethyl cyclohexene oxide (cis-trans mixture) in a yield of 4%. Purification of the reaction mixture by distillation yielded 31 g of 4,5-di-(vinyloxymethyl)cyclohexene oxide (cis-trans mixture) with a purity of 98%. Maintaining the temperature of the reaction mixture added dropwise fifteen minutes at 95° C After the completion of dropwise addition As the result of gas chromatography analysis of the mixture, it