3-(4-chlorophenoxy)propane-1,2-diol

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

Procedure: A mixture of 25.7 g (0.2 mole) of 4-chlorophenol, 18.5 g (0.25 mole) of glycidol and 1 ml of pyridine was stirred and heated at 85°-90° C. overnight. The pot residue was partitioned between ethyl ether and water. The organic layer was washed with water and brine, dried over sodium sulfate, and concentrated to give a gum which crystallized when triturated with petroleum ether (boiling point range, 30°-60° C.). The solid was collected by filtration and recrystallized from isopropyl ether to yield 27.2 g (67%) of off-white solid, mp 73°-75° C. (lit1 mp 77° C.). heated at 85°-90° C. overnight The pot residue was partitioned between ethyl ether and water The organic layer was washed with water and brine dried over sodium sulfate concentrated to give a gum which crystallized when triturated with petroleum ether (boiling point range, 30°-60° C.) The solid was collected by filtration recrystallized from isopropyl ether

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

Procedure: A mixture of 25.7 g (0.2 mole) of 4-chlorophenol, 18.5 g (0.25 mole) of glycidol and 1 ml of pyridine was stirred and heated at 85°-90° C. overnight. The pot residue was partitioned between ethyl ether and water. The organic layer was washed with water and brine, dried over sodium sulfate, and concentrated to give a gum which crystallized when triturated with petroleum ether (boiling point range, 30°-60° C.). The solid was collected by filtration and recrystallized from isopropyl ether to yield 27.2 g (67%) of off-white solid, mp 73°-75° C. (lit1 mp 77° C.). heated at 85°-90° C. overnight The pot residue was partitioned between ethyl ether and water The organic layer was washed with water and brine dried over sodium sulfate concentrated to give a gum which crystallized when triturated with petroleum ether (boiling point range, 30°-60° C.) The solid was collected by filtration recrystallized from isopropyl ether

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

Procedure: A mixture of 25.7 g (0.2 mole) of 4-chlorophenol, 18.5 g (0.25 mole) of glycidol and 1 ml of pyridine was stirred and heated at 85°-90° C. overnight. The pot residue was partitioned between ethyl ether and water. The organic layer was washed with water and brine, dried over sodium sulfate, and concentrated to give a gum which crystallized when triturated with petroleum ether (boiling point range, 30°-60° C.). The solid was collected by filtration and recrystallized from isopropyl ether to yield 27.2 g (67%) of off-white solid, mp 73°-75° C. (lit1 mp 77° C.). heated at 85°-90° C. overnight The pot residue was partitioned between ethyl ether and water The organic layer was washed with water and brine dried over sodium sulfate concentrated to give a gum which crystallized when triturated with petroleum ether (boiling point range, 30°-60° C.) The solid was collected by filtration recrystallized from isopropyl ether

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

Procedure: A mixture of 25.7 g (0.2 mole) of 4-chlorophenol, 18.5 g (0.25 mole) of glycidol and 1 ml of pyridine was stirred and heated at 85°-90° C. overnight. The pot residue was partitioned between ethyl ether and water. The organic layer was washed with water and brine, dried over sodium sulfate, and concentrated to give a gum which crystallized when triturated with petroleum ether (boiling point range, 30°-60° C.). The solid was collected by filtration and recrystallized from isopropyl ether to yield 27.2 g (67%) of off-white solid, mp 73°-75° C. (lit1 mp 77° C.). heated at 85°-90° C. overnight The pot residue was partitioned between ethyl ether and water The organic layer was washed with water and brine dried over sodium sulfate concentrated to give a gum which crystallized when triturated with petroleum ether (boiling point range, 30°-60° C.) The solid was collected by filtration recrystallized from isopropyl ether

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

Procedure: A mixture of 25.7 g (0.2 mole) of 4-chlorophenol, 18.5 g (0.25 mole) of glycidol and 1 ml of pyridine was stirred and heated at 85°-90° C. overnight. The pot residue was partitioned between ethyl ether and water. The organic layer was washed with water and brine, dried over sodium sulfate, and concentrated to give a gum which crystallized when triturated with petroleum ether (boiling point range, 30°-60° C.). The solid was collected by filtration and recrystallized from isopropyl ether to yield 27.2 g (67%) of off-white solid, mp 73°-75° C. (lit1 mp 77° C.). heated at 85°-90° C. overnight The pot residue was partitioned between ethyl ether and water The organic layer was washed with water and brine dried over sodium sulfate concentrated to give a gum which crystallized when triturated with petroleum ether (boiling point range, 30°-60° C.) The solid was collected by filtration recrystallized from isopropyl ether

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

Procedure: A mixture of 11.7 parts of 2-bromo-4'-chloroacetophenone, 12.2 parts of 1-(p-chlorophenoxy)-2,3-propanediol, 3 parts of p-toluenesulfonic acid and 240 parts of benzene is stirred and refluxed for 20 hours in a four-necked round-bottom flask equipped with a watertrap. The benzene solution is washed successively with a diluted sodium hydroxide solution and with water. The solvent is removed in vacuo. The residue is triturated in methanol. The precipitated product is filtered off (methanol filtrate is set aside) and crystallized from toluene, yielding A-2-(bromomethyl-4-(p-chlorophenoxymethyl)-2-(p-chlorophenyl)-1,3-dioxolane; m.p. 165°C. refluxed for 20 hours in a four-necked round-bottom flask equipped with a watertrap The benzene solution is washed successively with a diluted sodium hydroxide solution and with water The solvent is removed in vacuo The residue is triturated in methanol The precipitated product is filtered off (methanol filtrate crystallized from toluene

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

Procedure: A mixture of 25.7 g (3.2 mole) of 4-chlorophenol, 18.5 g (0.25 mole) of glycidol and 1 ml of pyridine was stirred and heated at 85°-90° C. overnight. The pot residue was partitioned between ethyl ether and water. The organic layer was washed with water and brine, dried over sodium sulfate, and concentrated to give a gum which crystallized when triturated with petroleum ether (boiling point range, 30°-60° C.). The solid was collected by filtration and recrystallized from isopropyl ether to yield 27.2 g (67%) of off-white solid, mp 73°-75° C. (lit1 mp 77° C.). heated at 85°-90° C. overnight The pot residue was partitioned between ethyl ether and water The organic layer was washed with water and brine dried over sodium sulfate concentrated to give a gum which crystallized when triturated with petroleum ether (boiling point range, 30°-60° C.) The solid was collected by filtration recrystallized from isopropyl ether

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

Procedure: A mixture of 25.7 g (0.2 mole) of 4-chlorophenol, 18.5 g (0.25 mole) of glycidol and 1 ml of pyridine was stirred and heated at 85°-90° C. overnight. The pot residue was partitioned between ethyl ether and water. The organic layer was washed with water and brine, dried over sodium sulfate, and concentrated to give a gum which crystallized when triturated with petroleum ether (boiling point range, 30°-60° C.). The solid was collected by filtration and recrystallized from isopropyl ether to yield 27.2 g (67%) of off-white solid, mp 73°-75° C. (lit1 mp 77° C.). heated at 85°-90° C. overnight The pot residue was partitioned between ethyl ether and water The organic layer was washed with water and brine dried over sodium sulfate concentrated to give a gum which crystallized when triturated with petroleum ether (boiling point range, 30°-60° C.) The solid was collected by filtration recrystallized from isopropyl ether