103633-32-5

Basic information

• Product Name: 3-C-(o-Benzyloxybenzyl)-4,6-dihydroxy-2-methoxyacetophenone
• CAS NO: 103633-32-5
• Molecular Weight: 378.425
• Mol File: 103633-32-5.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 3-C-(o-Benzyloxybenzyl)-4,6-dihydroxy-2-methoxyacetophenone(CAS DataBase Reference)
• NIST Chemistry Reference: 3-C-(o-Benzyloxybenzyl)-4,6-dihydroxy-2-methoxyacetophenone(103633-32-5)
• EPA Substance Registry System: 3-C-(o-Benzyloxybenzyl)-4,6-dihydroxy-2-methoxyacetophenone(103633-32-5)

Safety Data

• Hazardous Substances Data: 103633-32-5(Hazardous Substances Data)

Upstream product

• 5896-17-3 2-(phenylmethoxy)benzaldehyde 
• 90-02-8 salicylaldehyde 
• 100-44-7 benzyl chloride 
• 3381-87-1 2-benzyloxybenzyl alcohol 
• 3602-54-8 4,6-dihydroxy-2-methoxyacetophenone 
• 103633-30-3 2-bromomethylphenyl benzyl ether 

Downstream Products

• 103633-35-8 3'-C-(o-Benzyloxybenzyl)-4',6'-dibenzyloxy-2'-methoxychalcone 
• 61463-03-4 Isouvaretin 
• 103633-34-7 3-C-(o-Benzyloxybenzyl)-4,6-dibenzyloxy-2-methoxyacetophenone 

Relevant articles and documents

Aromatic Benzylation: Part III - Synthesis of Uvaretin, Isouvaretin and Related Nuclear Benzylated Dihydrochalcones

Reaction of 2-O-methylphloroacetophenone (5) with either o-benzyloxybenzyl alcohol (3) in the presence of boron trifluoride etherate and dioxan or with o-benzyloxybenzyl bromide (4) in the presence of methanolic potash affords 5-C-(o-benzyloxybenzyl) derivative (6) and its 3-C-isomer (7).Their orientation has been arrived at from a general behaviour of the chemical shift of chelated hydroxyl group in C-benzylated o-hydroxyacetophenones when C-benzyl group is present ortho or para to the chelated hydroxyl.Partial benzyl ether (9) of 6 and the complete benzyl ether (12) of 7 undergo facile condensation with benzaldehyde in the presence of alkali to give 10 and 13 respectively.These chalcones on hydrogenation in the presence of 10percent Pd-C afford uvaretin (11) and isouvaretin (14) respectively possessing physical characteristics identical with those of the natural samples.A parallel series of reactions starting from resacetophenone (15) provides C-benzylated dihydrochalcones 22 and 25 as analogues of uvaretin and isouvaretin respectively.