2-butoxypropan-1-ol

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: 2.0 g of LiAlH4 was added to 62 ml of ether and the mixture was stirred for 3 hours. To the mixture was added dropwise 12.7 g of (-)-ethyl-2-butoxypropionate in the same manner as in Example 1, and the mixture was stirred for 15 minutes. Then, 50 ml of water and 50 ml of 10% H2SO4 aqueous solution were added thereto. The ther layer was separated, dried with MgSO4 and filtrated. Ether was distilled off toobtain the objective product at an yield of 7.4 g. The optical rotation [α]D24° was +24.4°. the mixture was stirred for 15 minutes The ther layer was separated dried with MgSO4 filtrated Ether was distilled off toobtain the objective product at an yield of 7.4 g was +24.4°

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

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

Procedure: 2.0 g of LiAlH4 was added to 62 ml of ether and the mixture was stirred for 3 hours. To the mixture was added dropwise 12.7 g of (-)-ethyl-2-butoxypropionate in the same manner as in Example 1, and the mixture was stirred for 15 minutes. Then, 50 ml of water and 50 ml of 10% H2SO4 aqueous solution were added thereto. The ther layer was separated, dried with MgSO4 and filtrated. Ether was distilled off to obtain the objective product at an yield of 7.4 g. The optical rotation [α]D24° was +24.4°. the mixture was stirred for 15 minutes The ther layer was separated dried with MgSO4 filtrated Ether was distilled off to obtain the objective product at an yield of 7.4 g was +24.4°

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

Procedure: 40 g of dry pyridine and 15.3 g of 2-butoxypropanol were added into a four-necked flask and ice-cooled under stirring, and 35 g of p-toluenesulfonic acid chloride was added little by little to carry out the reaction for 2 hours. Then, the reaction mixture was returned to room temperature and the reaction was further carried out for 16 hours. The reaction product was added into ice-cooled 6% HCl aq. and the mixture was stirred. The mixture was then extracted with benzene and dried over anhydrous Na2SO4. Evaporation of benzene gave (2'-butoxypropyl)p-toluene sulfonate as an oily product. Yield: 33.2 g. The NMR data of this compound are shown below. ice-cooled the reaction for 2 hours was returned to room temperature The reaction product was added into ice- the mixture was stirred The mixture was then extracted with benzene dried over anhydrous Na2SO4 Evaporation of benzene

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

Procedure: 2.0 g of LiAlH4 was added to 100 ml of ether and the mixture was stirred for 3 hours, and 12.7 g of (-)-ethyl-2-butoxypropionate was added dropwise thereto. After completion of the dropwise addition, stirring was continued for 15 minutes. Then, 50 ml of water and 50 ml of an aqueous 10% H2SO4 were added. The ether layer was separated and dried over MgSO4. After filtration, ether was evaporated. Yield: 7.4 g, optical rotation [α]D24° =+24.4°. After completion of the dropwise addition stirring was continued for 15 minutes The ether layer was separated dried over MgSO4 After filtration, ether was evaporated Yield: 7.4 g, optical rotation [α]D24° =+24.4°

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

Procedure: 40 g of dry pyridine and 15.3 g of 2-butoxypropanol were added into a four-necked flask and ice-cooled under stirring, and 35 g of p-toluenesulfonic acid chloride was added little by little to carry out the reaction for 2 hours. Then, the reaction mixture was returned to room temperature and the reaction was further carried out for 16 hours. The reaction product was added into ice-cooled 6% HCl aq. and the mixture was stirred. The mixture was then extracted with benzene and dried over anhydrous Na2SO4. Evaporation of benzene gave (2'-butoxypropyl)p-toluene sulfonate as an oily product. Yield: 33.2 g. The NMR data of this compound are shown below. ice-cooled the reaction for 2 hours was returned to room temperature The reaction product was added into ice- the mixture was stirred The mixture was then extracted with benzene dried over anhydrous Na2SO4 Evaporation of benzene

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

Procedure: 2.0 g of LiAlH4 was added to 100 ml of ether and the mixture was stirred for 3 hours, and 12.7 g of (-)-ethyl-2-butoxypropionate was added dropwise thereto. After completion of the dropwise addition, stirring was continued for 15 minutes. Then, 50 ml of water and 50 ml of an aqueous 10% H2SO4 were added. The ether layer was separated and dried over MgSO4. After filtration, ether was evaporated. Yield: 7.4 g, optical rotation [α]D24° =+24.4°. After completion of the dropwise addition stirring was continued for 15 minutes The ether layer was separated dried over MgSO4 After filtration, ether was evaporated Yield: 7.4 g, optical rotation [α]D24° =+24.4°

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

Procedure: 2.0 g of LiAlH4 was added to 62 ml of ether and the mixture was stirred for 3 hours. To the mixture was added dropwise 12.7 g of (-)-ethyl-2-butoxypropionate in the same manner as in Example 1, and the mixture was stirred for 15 minutes. Then, 50 ml of water and 50 ml of 10% H2SO4 aqueous solution were added thereto. The ther layer was separated, dried with MgSO4 and filtrated. Ether was distilled off toobtain the objective product at an yield of 7.4 g. The optical rotation [α]D24° was +24.4°. the mixture was stirred for 15 minutes The ther layer was separated dried with MgSO4 filtrated Ether was distilled off toobtain the objective product at an yield of 7.4 g was +24.4°