[(1R,2R)-2-(hydroxymethyl)cyclohexyl]methanol

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

Procedure: To a solution of the compound (2) (71.86 g; 0.499 mol) and triethylamine (151.21 g; 1.497 mol) in chloroform (1 liter), methanesulfonyl chloride (114.27 g; 0.998 mol) is dropwise added under ice-cooling, and the resultant mixture is stirred at room temperature for 6 hours. The reaction mixture is washed with water, dried and concentrated under reduced pressure. Diethyl ether is added to the residue for crystallization, and the precipitated crystals are collected to give trans-1,2-bis(methanesulfonyloxymethyl)cyclohexane (3) (88.57 g). cooling The reaction mixture is washed with water dried concentrated under reduced pressure Diethyl ether is added to the residue for crystallization the precipitated crystals are collected

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

Procedure: To a mixture of lithium aluminum hydride (52.22 g; 1.374 mol) and tetrahydrofuran (500 ml), a solution of trans-1,2-cyclohexanedicarboxylic acid (5) (118.18 g; 0.687 mol) in tetrahydrofuran (2 liters) is dropwise added under reflux, and the resultant mixture is allowed to react under reflux for 3 hours. After completion of the reaction, the reaction mixture is cooled, and wet tetrahydrofuran and ether are dropwise added thereto, followed by filtraion. The filtrate is concentrated under reduced pressure to give trans-1,2-bis(hydroxymethyl)cyclohexane (2) (71.86 g). under reflux to react under reflux for 3 hours After completion of the reaction the reaction mixture is cooled The filtrate is concentrated under reduced pressure

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

Procedure: The thus obtained compound (2) (5.1 g; 35.4 mmol) is dissolved in triethylamine (10.37 g; 103 mmol) and acetonitrile (127 ml), and methanesulfonyl chloride (8.13 g; 71 mmol) is dropwise added thereto under ice-cooling. The resultant mixture is ice-cooled for 1 hour and allowed to react at room temperature for 3 hours. The reaction mixture is washed with water, dried and concentrated, followed by addition of diethyl ether. Precipitated crystals are collected by filtration to give trans-1,2-bis(methanesulfonyloxymethyl)cyclohexane (3) (5.4 g). under ice-cooling cooled for 1 hour to react at room temperature for 3 hours The reaction mixture is washed with water dried concentrated followed by addition of diethyl ether Precipitated crystals are collected by filtration

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

Procedure: To a mixture of lithium aluminum hydride (2.85 g; 75 mmol) and diethyl ether (50 ml), a solution of trans-1,2-cyclohexanedicarboxylic acid anhydride (1) (7.71 g; 50 mmol) in diethyl ether (150 ml) is dropwise added, and the resultant mixture is allowed to react at room temperature for 3 hours and then heated under reflux for 2 hours. After cooling, wet ether is dropwise added to the reaction mixture, followed by addition of water. The organic layer is collected by decantation, followed by concentration to give trans-1,2-bis(hydroxymethyl)cyclohexane (2) (5.1 g). to react at room temperature for 3 hours heated under reflux for 2 hours After cooling The organic layer is collected by decantation followed by concentration

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

Procedure: To a solution of the compound (2) (71.86 g; 0.499 mol) and triethylamine (151.21 g; 1.497 mol) in chloroform (1 liter), methanesulfonyl chloride (114.27 g; 0.998 mol) is dropwise added under ice-cooling, and the resultant mixture is stirred at room temperature for 6 hours. The reaction mixture is washed with water, dried and concentrated under reduced pressure. Diethyl ether is added to the residue for crystallization, and the precipitated crystals are collected to give trans-1,2-bis(methanesulfonyloxymethyl)cyclohexane (3) (88.57 g). cooling The reaction mixture is washed with water dried concentrated under reduced pressure Diethyl ether is added to the residue for crystallization the precipitated crystals are collected

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

Procedure: To a mixture of lithium aluminum hydride (52.22 g; 1,374 mol) and tetrahydrofuran (500 ml), a solution of trans-1,2-cyclohexanedicarboxylic acid (5) (118.18 g; 0.687 mol) in tetrahydrofuran (2 liters) is dropwise added under reflux, and the resultant mixture is allowed to react under reflux for 3 hours. After completion of the reaction, the reaction mixture is cooled, and wet tetrahydrofuran and ether are dropwise added thereto, followed by filtration. The filtrate is concentrated under reduced pressure to give trans-1,2-bis(hydroxymethyl)cyclohexane (2) (71.86 g). under reflux to react under reflux for 3 hours After completion of the reaction the reaction mixture is cooled followed by filtration The filtrate is concentrated under reduced pressure

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

Procedure: The thus obtained compound (2) (5.1 g; 35.4 mmol) is dissolved in triethylamine (10.37 g; 103 mmol) and acetonitrile (127 ml), and methanesulfonyl chloride (8.13 g; 71 mmol) is dropwise added thereto under ice-cooling. The resultant mixture is ice-cooled for 1 hour and allowed to react at room temperature for 3 hours. The reaction mixture is washed with water, dried and concentrated, followed by addition of diethyl ether. Precipitated crystals are collected by filtration to give trans-1,2-bis(methanesulfonyloxymethyl)cyclohexane (3) (5.4 g). under ice-cooling cooled for 1 hour to react at room temperature for 3 hours The reaction mixture is washed with water dried concentrated followed by addition of diethyl ether Precipitated crystals are collected by filtration

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

Procedure: To a mixture of lithium aluminum hydride (2.85 g; 75 mmol) and diethyl ether (50 ml), a solution of trans-1,2-cyclohexanedicarboxylic acid anhydride (1) (7.71 g; 50 mmol) in diethyl ether (150 ml) is dropwise added, and the resultant mixture is allowed to react at room temperature for 3 hours and then heated under reflux for 2 hours. After cooling, wet ether is dropwise added to the reaction mixture, followed by addition of water. The organic layer is collected by decantation, followed by concentration to give trans-1,2-bis(hydroxymethyl)cyclohexane (2) (5.1 g). to react at room temperature for 3 hours heated under reflux for 2 hours After cooling The organic layer is collected by decantation followed by concentration