95832-52-3Relevant academic research and scientific papers
Aromatic Benzylation: Part VI - Some More Experiments on Nuclear Benzylation of 2,4-Dihydroxydesoxybenzoin and Synthesis of C-Benzylated Isoflavones
Jain, A. C.,Nayyar, Naresh K.,Arya, P.
, p. 646 - 648 (2007/10/02)
2,4-Dihydroxydesoxybenzoin (1a) reacts with benzyl bromide in the presence of MeOH-KOH at room temperature to give 4-benzyl ether (1b) (31.4percent yield), 3-C-benzyl derivative (2a, 12.2percent), 5-C-benzyl derivative (3a, 2.8percent), 3,5-di-C-benzyl derivative (4a, 1.4percent) and 3-C-benzyl-4-benzyl ether (2b, 0.7percent).The desoxybenzoins 2a, 3a and 4a have also been converted into the corresponding C-benzylated isoflavones (5a, 5b and 5c).
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).
