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69877-38-9

(2E,4E)-5-(4-methoxy-2,3,6-trimethylphenyl)-3-methylpenta-2,4-dienal synthesis

14synthesis methods
-

Yield:69877-38-9 90%

Reaction Conditions:

with manganese(IV) oxide;sodium carbonate in dichloromethane at 25; for 1 h;

Steps:

4.1.5. General procedure for the MnO2-mediated oxidations of allylic alcohols

General procedure: To a vigorously stirred solution of alcohols 27-31 (2.2 mmol) in CH2Cl2 (45 mL), Na2CO3 (4.77 g, 45 mmol) and activated MnO2 powder (3.91 g, 45 mmol) were added. The resulting suspension was stirred at ambient temperature to complete the reaction (monitored by TLC) and then passed through a celite pad. The filtrate was evaporated to dryness to leave a residue. Allylic aldehydes 32-36 (only the 2E,4E-isomer is drawn) were obtained from this residue through FCC purification.

References:

Magoulas, George E.;Bariamis, Stavros E.;Athanassopoulos, Constantinos M.;Haskopoulos, Anastasios;Dedes, Petros G.;Krokidis, Marios G.;Karamanos, Nikos K.;Kletsas, Dimitris;Papaioannou, Dionissios;Maroulis, George [European Journal of Medicinal Chemistry,2011,vol. 46,# 2,p. 721 - 737] Location in patent:experimental part