Veratraldehyde → HCID 76168090, compound

HRID 1764740Notes

Reaction equation

[C:1]([C:4]1[C:5](=[O:15])[O:6][C:7]([OH:14])=[C:8]([C:11](=[O:13])[CH3:12])[C:9]=1[OH:10])(=[O:3])[CH3:2].COC1C=C(C=CC=1OC)C=O.[CH3:28][O:29][C:30]1[C:37]([O:38][CH3:39])=[CH:36][CH:35]=[CH:34][C:31]=1[CH:32]=O>>[C:11]([C:8]1[C:7](=[O:14])[O:6][C:5](=[O:15])[CH:4]([C:1](=[O:3])[CH:2]=[CH:32][C:31]2[CH:34]=[CH:35][CH:36]=[C:37]([O:38][CH3:39])[C:30]=2[O:29][CH3:28])[C:9]=1[OH:10])(=[O:13])[CH3:12]

Participants

Reactant 3

HCID 8419Veratraldehyde

HCID 665812,3-Dimethoxybenzaldehyde

HCID 1354659693,5-Diacetyl-2,6-dihydroxy-4h-pyran-4-one

Product 1

HCID 76168090HCID 76168090, compound

Procedure

Similarly, equimolar amounts of 3,5-diacetyl-4,6-dihydroxy-2H-pyran-2-one and 3,4-dimethoxybenzaldehyde or 2,3-dimethoxybenzaldehyde are reacted as above to yield the products, 5-acetyl-3-(3,4-dimethoxycinnamoyl)-4-hydroxy-2H-pyran-2,6(3H)-digne, m.p. 223°-225° C., and 5-acetyl-3-(2,3-dimethoxycinnamoyl)-4-hydroxy-2H-pyran-2,6(3H)-dione, m.p. 175°-176° C., respectively.

Sources & evidence

ORD record: ord-f4e3a16c40674b3aa341934d5314886a
Source dataset: uspto-grants-1978_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04117226

Reaction notes

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