Trifluoroacetic acid → 3-Methoxy-4-methoxycarbonylcinnamic acid

HRID 369892Notes

Reaction equation

HRID 369892 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:15]=[CH:16][C:17]=1[C:18]([O:20][CH3:21])=[O:19])[CH:6]=[CH:7][C:8]([O:10]C(C)(C)C)=[O:9].FC(F)(F)C(O)=O>ClCCl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:15]=[CH:16][C:17]=1[C:18]([O:20][CH3:21])=[O:19])[CH:6]=[CH:7][C:8]([OH:10])=[O:9]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 54318540HCID 54318540, compound

Product 1

HCID 543216923-Methoxy-4-methoxycarbonylcinnamic acidYield 44%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of t-butyl 3-methoxy-4-methoxycarbonylcinnamate (23.5 g) in anhydrous dichloromethane (100 ml) is added trifluoroacetic acid (50 ml) under ice-cooling, and the mixture is stirred at room temperature overnight. The reaction solution is concentrated under reduced pressure to remove the solvent, and the residue is crystallized from ethanol to give 3-methoxy-4-methoxycarbonylcinnamic acid (8.35 g).

Workup

  1. temperaturecooling
  2. concentrationThe reaction solution is concentrated under reduced pressure
  3. customto remove the solvent
  4. customthe residue is crystallized from ethanol

Sources & evidence

ORD record
ord-ea0a0cd91104483f8856bfa676c5f08a
Source dataset
uspto-grants-2000_10
Patent number
US06140330

Reaction notes

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