Réaction #164815

Équation de réaction

4-Hydroxy-3-methoxybenzaldehyde

4-hydroxy-3-methoxybenzaldehyde

potassium carbonate

Chloromethyl methyl ether

→

white solid

Rendement 99.2%

4-Methoxymethyloxy-3-methoxybenzaldehyde

Rendement 99.2%

Solvants

dimethyl formamide

Conditions de réaction

Traitement

1. 1
   workup.STIRRINGstirring
2. 2
   workup.WAITwas continued for 6 hr at room temperature
3. 3
   FiltrationThe resulting mixture was filtered
4. 4
   Extractionthe filtrate extracted into ethyl acetate
5. 5
   Lavagewashed with saturated sodium chloride
6. 6
   Séchagedried over magnesium sulfate
7. 7
   Filtrationfiltered
8. 8
   Autreevaporated

Mode opératoire

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.

Source