Vanillin → 3-(4-Hydroxy-3-methoxyphenyl)-1-(4-hydroxyphenyl)prop-2-en-1-one

HRID 1641606Notes

Reaction equation

[OH-].[K+].[OH:3][C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:12])[CH3:11])=[CH:6][CH:5]=1.O=[CH:14][C:15]1[CH:23]=[CH:22][C:20]([OH:21])=[C:17]([O:18][CH3:19])[CH:16]=1>C(OCCOCCOCC)C>[OH:21][C:20]1[CH:22]=[CH:23][C:15]([CH:14]=[CH:11][C:10]([C:7]2[CH:8]=[CH:9][C:4]([OH:3])=[CH:5][CH:6]=2)=[O:12])=[CH:16][C:17]=1[O:18][CH3:19]

Participants

Conditions

Temperature: 120 °C

Procedure

20 g of potassium hydroxide are initially introduced into 100 g of diethylene glycol diethyl ether, heated to 120° C. with stirring and combined with a mixture of 14 g of p-hydroxyacetophenone and 15 g of vanillin within 1 h. Once addition is complete, stirring is continued for a further 20 min, the mixture hydrolyzed and adjusted to pH 6-7. Once the phases have separated, the solvent is removed and 25 g of 3-(4-hydroxy-3-methoxyphenyl)-1-(4-hydroxyphenyl)-2-propen-1-one are obtained, yield: 93% of theoretical.

Workup

additionOnce addition
stirringstirring
customOnce the phases have separated
customthe solvent is removed

Sources & evidence

ORD record: ord-f7dbd4e15c9345b982098fb4efd4dfae
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08115033B2

Reaction notes

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