Acetophenone → Cinnamoylbenzene

HRID 2174420Notes

Reaction equation

HRID 2174420 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[OH-].[K+]>>[C:4]1([CH:1]=[CH:2][C:1]([C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)=[O:3])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

3

Reactant 2

HCID 7410AcetophenoneHCID 14797Potassium Hydroxide

Product 1

HCID 7189Cinnamoylbenzene

Procedure

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.

Sources & evidence

ORD record
ord-32a479aa15354c8bacbe39f0db86991c
Source dataset
uspto-grants-2015_06
Patent number
US09061984B2

Reaction notes

Loading…