Trifluoroacetic acid → 4-[1-Hydroxy-2-(methoxycarbonyl)ethyl]cinnamic acid

HRID 2227497Notes

Reaction equation

HRID 2227497 reaction equation
[OH:1][CH:2]([C:8]1[CH:27]=[CH:26][C:11]([CH:12]=[CH:13][C:14]([O:16]CC2C=CC(OC)=CC=2)=[O:15])=[CH:10][CH:9]=1)[CH2:3][C:4]([O:6][CH3:7])=[O:5].FC(F)(F)C(O)=O>C1(OC)C=CC=CC=1>[OH:1][CH:2]([C:8]1[CH:27]=[CH:26][C:11]([CH:12]=[CH:13][C:14]([OH:16])=[O:15])=[CH:10][CH:9]=1)[CH2:3][C:4]([O:6][CH3:7])=[O:5]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86758304HCID 86758304, compound

Product 1

HCID 701562264-[1-Hydroxy-2-(methoxycarbonyl)ethyl]cinnamic acidYield 91%

Reagents, catalysts & solvents 1

HCID 7519AnisoleSolvent

Procedure

44 mg of p-anisyl 4-[1-hydroxy-2-(methoxycarbonyl)ethyl]cinnamate was dissolved in 0.1 ml anisole, and then treated with 0.1 ml trifluoroacetic acid on ice for 30 minutes to give 4-[1-hydroxy-2-(methoxycarbonyl)ethyl]cinnamic acid (27 mg, 91%) as a white solid.

Sources & evidence

ORD record
ord-c365f17cf67841189b24c30ba918c4d6
Source dataset
uspto-grants-2002_07
Patent number
US06413995B1

Reaction notes

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