Pyridine → 1-Chloroethyl Hexyl Carbonate

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Reaction Steps

1-Chloroethyl chloroformate (10.0 g, 69.9 mmol) and 1-hexanol (6.5 g, 63.6 mmol) were dissolved in chloroform (80 ml) at 0° C. Pyridine (5.5 g, 69.5 mmol) was added dropwise during 17 minutes maintaining the temperature below 10° C. After stirring at room temperature for 20 hours the organic phase was washed three times with 1 normal hydrochloric acid, once with a saturated sodium hydrogen carbonate solution and finally twice with water. The organic solution was dried with magnesium sulfate and the solvent was removed at reduced pressure. The residue (11.6 g) was distilled in vacuo (Bp. 61°-72° C., 3×10-3 mbar). Yield: 9.0 g. 1H-NMR (CDCl3): delta=0.89 (CH2CH3); 1.28-1.40 (CH2CH2CH×2CH3); 1.69 (OCH2CH2); 1.83 (CH3CH); 4.20 (OCH2); 6.43 ppm (CH).

Provenance & Evidence