Veratraldehyde → 1-(3,4-Dimethoxyphenyl)-2,3-bis(ethoxycarbonyl)-4-hydroxy-6,7,8-trimethoxynaphthalene

HRID 622458

Reaction equation

CO[CH:3]([O:17]C)[C:4]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([O:12][CH3:13])=[C:6]([O:14][CH3:15])[C:5]=1Br.[CH3:19][O:20][C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][C:28]=1[O:29][CH3:30])[CH:24]=O.[C:31]([C:38]([O:40][CH2:41][CH3:42])=[O:39])#[C:32][C:33]([O:35][CH2:36][CH3:37])=[O:34]>>[CH3:19][O:20][C:21]1[CH:22]=[C:23]([C:24]2[C:5]3[C:4](=[CH:9][C:8]([O:10][CH3:11])=[C:7]([O:12][CH3:13])[C:6]=3[O:14][CH3:15])[C:3]([OH:17])=[C:32]([C:33]([O:35][CH2:36][CH3:37])=[O:34])[C:31]=2[C:38]([O:40][CH2:41][CH3:42])=[O:39])[CH:26]=[CH:27][C:28]=1[O:29][CH3:30]

Participants

Reactant 3

HCID 8419Veratraldehyde

HCID 69803Diethyl acetylenedicarboxylate

HCID 159144582-Bromo-3,4,5-trimethoxybenzaldehyde dimethylacetal

Product 1

HCID 105777341-(3,4-Dimethoxyphenyl)-2,3-bis(ethoxycarbonyl)-4-hydroxy-6,7,8-trimethoxynaphthalene

Procedure

2-Bromo-3,4,5-trimethoxybenzaldehyde dimethylacetal, 3,4-dimethoxybenzaldehyde and diethyl acetylenedicarboxylate are treated in the same manner as described in Example 1-(1) and (2), whereby 1-(3,4-dimethoxyphenyl-2,3-bis(ethoxycarbonyl)-4-hydroxy-6,7,8-trimethoxynaphthalene is obtained as colorless crystals.

Sources & evidence

ORD record: ord-6b3c5ef8608443f7a19e6e37c842cb59
Source dataset: uspto-grants-1988_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04771072

Linked notes

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