93898-99-8Relevant academic research and scientific papers
Aromatic Benzylation: Part V - Synthesis of Nuclear Benzylated Chalcones and Dihydrochalcones from Gallacetophenone and β-Resacetophenone as Analogues of Uvaretin and Isouvaretin
Jain, A. C.,Nayyar, Naresh K.,Arya, P.
, p. 259 - 263 (2007/10/02)
5-C-Benzylgallacetophenone (1b) has been prepared in two ways: (i) by treating gallacetophenone (1a) with benzyl alcohol in the presence of BF3-Et2O and (ii) by the Claisen rearrangement of 3,4-di-O-benzylgallacetophenone (1d) in TFA at room temperature.P
Aromatic Benzylation of 2,4-Dihydroxybenzoyl Derivatives and Synthesis of C-Benzylated Chromone, Isoflavone and Coumarin Derivatives
Jain, A. C.,Arya, P.,Nayyar, N. K.
, p. 1030 - 1035 (2007/10/02)
2,4-Dihydroxyacetophenone (1a) when reacted with benzyl alcohol in the presence of boron trifluoride etherate and dioxan affords a mixture of 5C-benzyl (2a; major component), 3C- (3a) and 3,5-di-C (4a) derivatives.The monobenzyl derivatives (2a and 3a) are also formed in similar proportions by keeping 2-hydroxy-4-benzyloxyacetophenone (5) with trifluoroacetic acid at room temperature for 70 hr.The above reactions when carried out on 2,4-dihydroxydesoxybenzoin (1c) and its 4-benzyl ether (6) yield the corresponding products (2c, 3c and 4c) in similar amounts.The Perkin reaction on C-benzylated acetophenones (2a, 3a and 4a) with Ac2O-NaOAc furnishes the corresponding 7-acetoxy-3-acetyl-C-benzyl-2-methylchromones (7a, 8a and 9a); whereas the same reaction on C-benzylated desoxybenzoins (2c, and 4c) gives 7-acetoxy-6C-benzyl-2-methylisoflavones (7b and 9b).Compound (2c) has also been converted into 6C-benzyl-4,7-dihydroxy-3-phenylcoumarin (11).
