3-(3,4-Dihydroxyphenyl)Prop-2-Enoic Acid → Acetoacetic Acid

HRID 1157053

Reaction equation

HRID 1157053 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[OH:13])[CH:5]=[CH:6][C:7]([OH:9])=[O:8].C([O:17][C:18](=[O:20])[CH3:19])(=O)C>N1C=CC=CC=1>[OH:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[OH:13])[CH:5]=[CH:6][C:7]([OH:9])=[O:8].[CH3:12][C:2]([CH2:19][C:18]([OH:17])=[O:20])=[O:1]

Participants

5

Reactant 2

HCID 25183-(3,4-Dihydroxyphenyl)Prop-2-Enoic AcidHCID 7918Acetic Anhydride

Product 2

HCID 96Acetoacetic AcidHCID 25183-(3,4-Dihydroxyphenyl)Prop-2-Enoic Acid

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In accordance with the above flowchart, 3,4-dihydroxycinnamic acid (1) is reacted with acetic anhydride in pyridine for 18-30 hours and then extracted with organic solvents, giving 3,4-dihydroxycinnamic acid, diacetate (2) which is further converted to the 3,4-dihydroxycinnamic acid chloride (3) by treatment with thionyl chloride in dimethylformamide at -20° to -18° C. for 30-90 minutes.

Workup

  1. extractionextracted with organic solvents

Sources & evidence

ORD record
ord-602d0fb017934ef19c0aecd7ceace79c
Source dataset
uspto-grants-1982_06
Patent number
US04337249

Linked notes

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