Hydrogen Bromide → 3-(3,4-Dihydroxybenzoyl)propionic acid
Reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([CH:13]=[CH:14][C:15]=1[O:16]C)[C:6]([CH2:8][CH2:9][C:10]([OH:12])=[O:11])=[O:7].Br>>[OH:2][C:3]1[CH:4]=[C:5]([CH:13]=[CH:14][C:15]=1[OH:16])[C:6]([CH2:8][CH2:9][C:10]([OH:12])=[O:11])=[O:7]Participants
3
Procedure
A 5-carboxymethyl-4-(3,4-disubstituted phenyl)-2-mercaptothiazole derivative can be produced by reacting veratrole with succinic anhydride in the presence of anhydrous aluminum chloride to obtain 3-(3,4-dimethoxybenzoyl)propionic acid, subjecting the propionic acid to demethylation with hydrobromic acid to obtain 3-(3,4-dihydroxybenzoyl)propionic acid, then, subjecting it to enol-lactonation in the presence of acetic anhydride and sodium acetate, reacting the resulting compound sequentially with N-bromosuccinimide and with diphenyldiazomethane to obtain 3-(3,4-diacetoxybenzoyl)-3-bromopropionate, and reacting the propionate with ammonium dithiocarbamate to obtain the desired product.
Sources & evidence
- ORD record
- ord-312c357ffbc143bcb543dacc4f5346f3
- Source dataset
- uspto-grants-1991_10
- Patent number
- US05061794
Reaction notes
Loading…