반응 #164815

반응 방정식

4-Hydroxy-3-methoxybenzaldehyde

4-hydroxy-3-methoxybenzaldehyde

potassium carbonate

Chloromethyl methyl ether

→

white solid

수율 99.2%

4-Methoxymethyloxy-3-methoxybenzaldehyde

수율 99.2%

용매

dimethyl formamide

반응 조건

후처리

1. 1
   workup.STIRRINGstirring
2. 2
   workup.WAITwas continued for 6 hr at room temperature
3. 3
   여과The resulting mixture was filtered
4. 4
   추출the filtrate extracted into ethyl acetate
5. 5
   세척washed with saturated sodium chloride
6. 6
   건조dried over magnesium sulfate
7. 7
   여과filtered
8. 8
   기타evaporated

실험 절차

4-Hydroxy-3-methoxybenzaldehyde (1a, 2.00 g, 13.1 mmol) and potassium carbonate (9.00 g, 65.1 mmol) were combined in dimethyl formamide (30 ml) and stirred for 15 min at room temperature. Chloromethyl methyl ether (1.60 ml, 21.1 mmol) was added and stirring was continued for 6 hr at room temperature. The resulting mixture was filtered and the filtrate extracted into ethyl acetate, washed with saturated sodium chloride, dried over magnesium sulfate, filtered and evaporated to give 2.55 g (99%) of a white solid: mp 39-40° C. [expected mp 41° C.]; 1H NMR: δ 3.40 (s, 3H), 3.83 (s, 3H), 5.21 (s, 2H), 7.15 (d, 1H, J=8.7 Hz), 7.30 (dd, 1H, J=6.0, 2.0 Hz), 7.32 (s, 1H), 9.75 (s, 1H); 13C NMR: δ 55.8, 56.2, 94.8, 109.4, 114.6, 125.9, 130.9, 149.8, 151.7, 190.4.

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