Acetophenone → Cinnamoylbenzene

Participants

Reaction Steps

In some embodiments Scheme A can include reaction sequences as follows: Initially, 2,4,6-trihydroxyacetophenone is transformed into 2,4-dihydroxy-6-methoxyacetophenone using dimethyl sulphate as methylating agent. Then, the methyl group on the para-methoxy position of the acetophenone is cleaved using AlCl3, to obtain 2,4-dihydroxy-6-methoxyacetophenone, which is protected using allyl bromide to give 2,4-allyloxy-6-methoxylacetophenone. Claisen-Schmidt aldol condensation of acetophenone with the corresponding aromatic aldehyde in the presence of aqueous KOH, gives a chalcone product. After a mild deprotection procedure to remove the allyl-protecting groups, using Pd(PPh3)4 and K2CO3, the resulting 2′4′-dihydroxy-6-methoxy chalcones were finally reduced to produce the corresponding dihydrochalcones.

Provenance & Evidence