Reaktion #9038

Reaktionsgleichung

dimethyl sulfate

ethyl 6-methylsalicylate

lithium hydroxide monohydrate

→

ethyl 2-methoxy-6-methylbenzoate

Ausbeute 91.0%

Lösungsmittel

diethyl ether

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturto reflux for 1 hour
2. 2
   Waschenwashed with saturated aqueous NaHCO3 (4×10 mL)
3. 3
   Trocknendried (MgSO4)
4. 4
   Einengenconcentrated
5. 5
   SonstigePurification of the crude material by column chromatography on silica gel (9:1 hexanes-EtOAc)

Vorschrift

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).

Quelle