Methyl-P-Coumarate → Methyl 4-(2,3,4,5-tetramethoxy-6-methylbenzyloxy)cinnamate

HRID 580237Notes

Reaction equation

HRID 580237 reaction equation
[CH3:1][O:2][C:3]1[C:8]([CH2:9]Br)=[C:7]([CH3:11])[C:6]([O:12][CH3:13])=[C:5]([O:14][CH3:15])[C:4]=1[O:16][CH3:17].[CH3:18][O:19][C:20](/[CH:22]=[CH:23]/[C:24]1[CH:25]=[CH:26][C:27]([OH:30])=[CH:28][CH:29]=1)=[O:21]>>[CH3:1][O:2][C:3]1[C:4]([O:16][CH3:17])=[C:5]([O:14][CH3:15])[C:6]([O:12][CH3:13])=[C:7]([CH3:11])[C:8]=1[CH2:9][O:30][C:27]1[CH:26]=[CH:25][C:24]([CH:23]=[CH:22][C:20]([O:19][CH3:18])=[O:21])=[CH:29][CH:28]=1.[CH3:1][O:2][C:3]1[C:4]([O:16][CH3:17])=[C:5]([O:14][CH3:15])[C:6]([O:12][CH3:13])=[C:7]([CH3:11])[C:8]=1[CH2:9][O:30][C:27]1[CH:26]=[CH:25][C:24]([CH:23]=[CH:22][C:20]([OH:21])=[O:19])=[CH:29][CH:28]=1

Participants

4

Reactant 2

HCID 5319562Methyl-P-CoumarateHCID 148523231-(Bromomethyl)-2,3,4,5-tetramethoxy-6-methylbenzene

Product 2

HCID 53711833Methyl 4-(2,3,4,5-tetramethoxy-6-methylbenzyloxy)cinnamateHCID 544705014-(2,3,4,5-Tetramethoxy-6-methylbenzyloxy)cinnamic acid

Procedure

Using 1,2,3,4-tetramethoxy-5-methyl-6-bromomethylbenzene and methyl p-hydroxycinnamate and following the procedure described above, there were obtained methyl 4-(2,3,4,5-tetramethoxy-6-methylbenzyloxy)cinnamate (Compound 13) and 4-(2,3,4,5-tetramethoxy-6-methylbenzyloxy)cinnamic acid (Compound 14).

Sources & evidence

ORD record
ord-e22a21df045d4949b718dbaafb1d49b2
Source dataset
uspto-grants-1988_06
Patent number
US04751303

Reaction notes

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