18-Crown-6 → Phenyl Fluoroformate

Reaction equation

[C:1](=O)([O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[O:2]C(Cl)C.[F-:14].[K+].C1OCCOCCOCCOCCOCCOC1>>[F:14][C:1]([O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:2]

Participants

Reactant 3

HCID 2855718-Crown-6

HCID 522689Potassium Fluoride

HCID 135570931-Chloroethyl phenyl carbonate

Product 1

HCID 11815898Phenyl FluoroformateYield 70%

Conditions

Temperature: 75 °C

Procedure

A mixture of 11.6 g (0.058 mole) of freshly distilled 1-chloroethyl phenyl carbonate, 4.60 g (0.079 mole) of anhydrous KF (Aldrich), 0.80 g (0.003 mole) of 18-crown-6 ether (Aldrich) is prepared. The mixture is stirred and heated by means of an oil bath at 75° C. at a pressure of about 2.7 kPa. The reaction is allowed to proceed for 90 minutes during which the phenyl fluoroformate which is formed continuously evaporates and is removed by fractional distillation.