Ethyl Acetate → 3',4'-Didemethylnobiletin

Reaction equation

C(OCC)(=O)C.C([O:14][C:15]1[CH:16]=[C:17]([CH:37]=[CH:38][C:39]=1[O:40]CC1C=CC=CC=1)[C:18]1[O:19][C:20]2[C:25]([C:26](=[O:28])[CH:27]=1)=[C:24]([O:29][CH3:30])[C:23]([O:31][CH3:32])=[C:22]([O:33][CH3:34])[C:21]=2[O:35][CH3:36])C1C=CC=CC=1>[Pd].CO>[OH:14][C:15]1[CH:16]=[C:17]([CH:37]=[CH:38][C:39]=1[OH:40])[C:18]1[O:19][C:20]2[C:25]([C:26](=[O:28])[CH:27]=1)=[C:24]([O:29][CH3:30])[C:23]([O:31][CH3:32])=[C:22]([O:33][CH3:34])[C:21]=2[O:35][CH3:36]

Participants

Procedure

Into 200 ml. of a mixed solvent of ethyl acetate and methanol at a ratio of 1:1 was dissolved 1.11 g. of 3',4'-bis(benzyloxy)-5,6,7,8-tetramethoxyflavone and added 0.2 to 0.3 g. of 10% palladium-charcoal. The resulting mixture was mixed with shaking in a stream of H2 gas until H2 absorption was completed. After filtering out the catalyst, the obtained filtrate was concentrated. The residue was recrystallized from methanol to give 0.74 g. (97% of the theoretical amount) of the desired compound being a colorless prismatic crystal.