117845-75-7Relevant academic research and scientific papers
A Study of α-C-Benzylation of 2-Hydroxydesoxybenzoins
Jain, A. C.,Shrivastava, Rene,Tyagi, O. D.
, p. 625 - 628 (2007/10/02)
Benzylation of three 2-hydroxy-methoxydesoxybenzoins (1a, 1b and 1c) with benzyl chloride (1 mol) in the presence of potassium iodide, potassium carbonate and acetone under dry refluxing conditions for 6 hr affords only α-C-benzyl derivatives (2a, 2b and 2c, repectively) without any O-benzylation in yields from 34 to 54percent.But, in the presence of a more polar solvent DMF under similar conditions O-benzylation also occurs giving a mixture of products.Benzylation of 2,4-dihydroxydesoxybenzoin (5) with benzyl bromide in acetone medium reveals that 4-O-benzylation is the first step followed by α-C-benzylation or O-benzylation; further no aromatic benzylation occurs.Finally it has been found that the yield of α-C-benzylated product increases up to 71percent if a non-polar solvent THF is used in the presence of sodium hydride.
