Methyl iodide → HCID 53795816, compound

HRID 894150Notes

Reaction equation

HRID 894150 reaction equation
[C@@H:1]1([OH:6])[CH2:4][CH2:3][C@@H:2]1[OH:5].[F:7][C:8]1[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=1[CH2:10]Cl.[OH-].[Na+].[CH3:18]I>CS(C)=O>[F:7][C:8]1[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=1[CH2:10][O:5][C@@H:2]1[CH2:3][CH2:4][C@@H:1]1[O:6][CH3:18]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 9580Benzene, 1-(chloromethyl)-2-fluoro-HCID 14798Sodium Hydroxide2×HCID 13215602HCID 13215602, compound

Product 1

HCID 53795816HCID 53795816, compoundYield 88.9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

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.

Workup

  1. temperaturewhilst cooling with ice
  2. temperaturewhilst cooling
  3. stirringThereafter, the reaction mixture was again stirred at room temperature for 6 hours
  4. extractionThe mixture was extracted three times with 5 liters of petroleum ether each time
  5. dry with materialthe combined organic phases were dried over sodium sulphate
  6. concentrationconcentrated
  7. distillationby distilling off the solvent

Sources & evidence

ORD record
ord-6511cefe66a34f67b9747b46a63c9f90
Source dataset
uspto-grants-1981_08
Patent number
US04282388

Reaction notes

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