(1S,2R)-cyclobutane-1,2-diol

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

Procedure: 396.0 g. (4.5 mol) of cis-1,2-cyclobutanediol and 650.3 g (4.5 mol) of 2-fluorobenzyl chloride were dissolved in 2.5 liters of dimethylsulphoxide, and 270 g (6.75 mol) of sodium hydroxide powder were added in portions at room temperature, whilst cooling with ice. The mixture was stirred at room temperature for 6 hours and 958.5 g (6.75 mol) of methyl iodide and, in portions, 270 g (6.75 mol) of sodium hydroxide powder were then added, whilst cooling. Thereafter, the reaction mixture was again stirred at room temperature for 6 hours and discharged onto 10 liters of ice-water. The mixture was extracted three times with 5 liters of petroleum ether each time and the combined organic phases were dried over sodium sulphate and concentrated by distilling off the solvent. 840 g (88.9% of theory) of cis-1-(2-fluorobenzyloxy)-2-methoxy-cyclobutane of refractive index nD21 =1.4948 were obtained. whilst cooling with ice whilst cooling Thereafter, the reaction mixture was again stirred at room temperature for 6 hours The mixture was extracted three times with 5 liters of petroleum ether each time the combined organic phases were dried over sodium sulphate concentrated by distilling off the solvent

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

Procedure: 396.0 g. (4.5 mol) of cis-1,2-cyclobutanediol and 650.3 g (4.5 mol) of 2-fluorobenzyl chloride were dissolved in 2.5 liters of dimethylsulphoxide, and 270 g (6.75 mol) of sodium hydroxide powder were added in portions at room temperature, whilst cooling with ice. The mixture was stirred at room temperature for 6 hours and 958.5 g (6.75 mol) of methyl iodide and, in portions, 270 g (6.75 mol) of sodium hydroxide powder were then added, whilst cooling. Thereafter, the reaction mixture was again stirred at room temperature for 6 hours and discharged onto 10 liters of ice-water. The mixture was extracted three times with 5 liters of petroleum ether each time and the combined organic phases were dried over sodium sulphate and concentrated by distilling off the solvent. 840 g (88.9% of theory) of cis-1-(2-fluorobenzyloxy)-2-methoxy-cyclobutane of refractive index nD21 =1.4948 were obtained. whilst cooling with ice whilst cooling Thereafter, the reaction mixture was again stirred at room temperature for 6 hours The mixture was extracted three times with 5 liters of petroleum ether each time the combined organic phases were dried over sodium sulphate concentrated by distilling off the solvent