Veratraldehyde → Dimethyl 8-(3,4-dimethoxyphenyl)-5-hydroxybenzo[f][1,3]benzodioxole-6,7-dicarboxylate

HRID 330569Notes

Reaction equation

CO[CH:3]([O:14]C)[C:4]1[CH:9]=[C:8]2[O:10][CH2:11][O:12][C:7]2=[CH:6][C:5]=1Br.[CH3:16][O:17][C:18]1[CH:19]=[C:20]([CH:23]=[CH:24][C:25]=1[O:26][CH3:27])[CH:21]=O.[C:28]([C:34]([O:36][CH3:37])=[O:35])#[C:29][C:30]([O:32][CH3:33])=[O:31]>>[CH3:16][O:17][C:18]1[CH:19]=[C:20]([C:21]2[C:5]3[C:4](=[CH:9][C:8]4[O:10][CH2:11][O:12][C:7]=4[CH:6]=3)[C:3]([OH:14])=[C:29]([C:30]([O:32][CH3:33])=[O:31])[C:28]=2[C:34]([O:36][CH3:37])=[O:35])[CH:23]=[CH:24][C:25]=1[O:26][CH3:27]

Participants

Reactant 3

HCID 8419Veratraldehyde

HCID 12980Dimethyl acetylenedicarboxylate

HCID 110549061,3-Benzodioxole, 5-bromo-6-(dimethoxymethyl)-

Product 1

HCID 10599219Dimethyl 8-(3,4-dimethoxyphenyl)-5-hydroxybenzo[f][1,3]benzodioxole-6,7-dicarboxylate

Procedure

2-Bromo-4,5-methylenedioxybenzaldehyde dimethyl-acetal, 3,4-dimethoxybenzaldehyde and dimethyl acetylene-dicarboxylate are treated in the same manner as described in Example 1, whereby 1-(3,4-dimethoxyphenyl)-2,3-bis-(methoxycarbonyl)-4-hydroxy-6,7-methylenedioxynaphthalene is obtained as colorless crystals.

Sources & evidence

ORD record: ord-2280d0cced4c44679a445eff14aec412
Source dataset: uspto-grants-1990_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04897418

Reaction notes

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