98498-19-2

Upstream product

• 93-97-0 benzoic acid anhydride 
• 103865-37-8 3-diphenylmethyl-2,4,6-trihydroxyacetophenone 
• 91-01-0 1,1-Diphenylmethanol 
• 480-40-0 5,7-dihydroxy-2-phenyl-chromen-4-one 

Downstream Products

• 98498-23-8 5-hydroxy-7-methoxy-6-(diphenylmethyl)flavone 
• 98498-20-5 Acetic acid 7-acetoxy-6-benzhydryl-4-oxo-2-phenyl-4H-chromen-5-yl ester 
• 103865-60-7 Acetic acid 6-benzhydryl-5-hydroxy-4-oxo-2-phenyl-4H-chromen-7-yl ester 

Relevant academic research and scientific papers

Aromatic Benzhydrylation: Part IV - Syntheses of Triarylmethane Group of Chalcones, Flavanones, Flavones, Chromones and 2-Methylchromones using Benzhydrylation of Phloroacetophenone, Gallacetophenone and 5,7-Dihydroxyflavanones

Phloroacetophenone reacts with diphenylcarbinol in the presence of BF3-C2H5OC2H5 to give its 3-diphenylmethyl (2d, 25percent yield) and 3,5-bisdiphenylmethyl derivatives (2e, 17.4percent yield) along with a small amount of dibenzhydryl ether (1). 2d on either heating with Ac2O-NaOAc at 180 deg C or treating with CH3SO2Cl, DMF and BF3-C2H5OC2H5 affords only the corresponding 6-diphenylmethylchromone (3b or 5f) as established by PMR data and direct comparison with an authentic sample.A similar reaction of 2a yields 3a and 5a.Alkaline hydrolysis of 3a and 3b gives the corresponding benzhydrylated 2-methylchromones (4a and 4f).Compounds 2b and 2e have been converted into benzhydrylated chalcones (6a and 6b respectively) and flavones (8a and 8f respectively) by standard methods without any difficulty.However, isomerisation of 6a gives the flavanone 7c in a poor yield.A better method of preparing benzhydrylated flavanones involves direct benzhydrylation of hydroxyflavanones.Thus, 5,7-dihydroxyflavanone (7l) gives a separable mixture of 7a, 7f and 7j.Gallacetophenone on benzhydrylation gives mainly its 5-diphenylmethylderivative (9a) which can be converted into the corresponding chromones (11a and 11c) and chalcone (10).Structures of all the products have been established by elemental analysis and PMR data.

Aromatic Benzhydrylation: Part II - Synthesis of Triarylmethane Groups of Flavones and Flavonols Involving Aromatic Benzhydrylation of Chrysin and 3-O-Methylgalangin

Chrysin (1) when treated with diphenylcarbinol in the presence of boron-trifluoride etherate and dioxan yields 6-diphenylmethyl derivative (2a) as the major product (23percent) along with 8-diphenylmethyl (3a, 19percent) and 6,8-bis(diphenylmethyl) (4a, 1