تفاعل #579316

معادلة التفاعل

chloroacetyl chloride

(−)-menthol

pyridine

→

(−)-menthyl chloroacetate

المردود 94.7%

المذيبات

diethyl ether

diethyl ether

ظروف التفاعل

المعالجة

1. 1
   ترشيحthe resulting mixture was then filtered
2. 2
   غسيلThe filtrate was washed with HCl (60 mL, 2 N)
3. 3
   تجفيفNaHCO3 (60 mL), brine and dried with Na2SO4
4. 4
   أخرىRemoval of the solvent
5. 5
   أخرىdrying under vacuum

الإجراء التجريبي

A solution of chloroacetyl chloride (6.4 mL, 80 mmol) in 40 mL anhydrous diethyl ether was added dropwise within 2 h to a solution of (−)-menthol (3a) (12.5 g, 80 mmol) and pyridine (6.5 mL, 80 mmol) in anhydrous diethyl ether (160 mL) at 0° C. After warming to RT, the white suspension was stirred for 2 h and the resulting mixture was then filtered. The filtrate was washed with HCl (60 mL, 2 N), saturated. NaHCO3 (60 mL), brine and dried with Na2SO4. Removal of the solvent and drying under vacuum afford (−)-menthyl chloroacetate (4a) (17.64 g, 94%), which was used without further purification. U.S. Pat. No. 4,456,611; Helv. Chim. Acta 1988, 71, 1553.

المصدر