تفاعل #9038

معادلة التفاعل

dimethyl sulfate

ethyl 6-methylsalicylate

lithium hydroxide monohydrate

→

ethyl 2-methoxy-6-methylbenzoate

المردود 91.0%

المذيبات

diethyl ether

THF

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةto reflux for 1 hour
2. 2
   غسيلwashed with saturated aqueous NaHCO3 (4×10 mL)
3. 3
   تجفيفdried (MgSO4)
4. 4
   تركيزconcentrated
5. 5
   أخرىPurification of the crude material by column chromatography on silica gel (9:1 hexanes-EtOAc)

الإجراء التجريبي

To a solution of ethyl 6-methylsalicylate (1.27 g, 6.97 mmol) in THF (35 mL) was added lithium hydroxide monohydrate (0.594 g, 14.2 mmol) followed by dimethyl sulfate (1.00 mL, 10.6 mmol). The resultant mixture was heated to reflux for 1 hour then cooled to room temperature. The mixture was diluted with diethyl ether (70 mL), washed with saturated aqueous NaHCO3 (4×10 mL), dried (MgSO4) and concentrated. Purification of the crude material by column chromatography on silica gel (9:1 hexanes-EtOAc) provided 1.23 g (91%) of ethyl 2-methoxy-6-methylbenzoate as a white solid. 1H NMR (CDCl3) δ 1.38 (t, 3H, J=7.2 Hz), 2.30 (s, 3H), 3.82 (s, 3H), 4.40 (q, 2H, J=7.2 Hz), 6.76 (d, 1H, J=8.4 Hz), 6.79 (d, 1H, J=7.8 Hz), 7.23 (dd, 1H, J=7.8, 8.4 Hz).

المصدر