Diethyl Ether → (Oxiran-2-yl)methyl 2-fluorobenzoate

HRID 1995101Notes

Reaction equation

HRID 1995101 reaction equation
[CH2:1]1[O:3][CH:2]1[CH2:4][OH:5].CCOCC.[F:11][C:12]1[CH:20]=[CH:19][CH:18]=[CH:17][C:13]=1[C:14](Cl)=[O:15]>N1C=CC=CC=1>[F:11][C:12]1[CH:20]=[CH:19][CH:18]=[CH:17][C:13]=1[C:14]([O:5][CH2:4][CH:2]1[O:3][CH2:1]1)=[O:15]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 98082-Fluorobenzoyl chlorideHCID 11164Glycidol

Product 1

HCID 13475609(Oxiran-2-yl)methyl 2-fluorobenzoateYield 71%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
25 °C

Procedure

A mixture containing 37 g (0.5 mole) of glycidol, 500 ml of anhydrous ether, 500 ml of pyridine and 80 g (0.5 mole) of o-fluoro-benzoyl chloride was stirred at 0° C. for 1 hour and 25° C. for 2 hours. The mixture was filtered and the ethanol filtrate was washed with 100 ml of 5% HCl. Evaporation of the ether gave an oil which was distilled to give 69.5 g (71%) of product, b.p. 115° C./0.5 mmHg. The NMR and IR spectra were consistent with the assigned structure.

Workup

  1. filtrationThe mixture was filtered
  2. washthe ethanol filtrate was washed with 100 ml of 5% HCl
  3. customEvaporation of the ether
  4. customgave an oil which
  5. distillationwas distilled

Sources & evidence

ORD record
ord-557da2b465fc4fecb5bde02287980eef
Source dataset
uspto-grants-1983_09
Patent number
US04402974

Reaction notes

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