Trifluoroacetic acid → HCID 45122633, compound

HRID 1640072Notes

Reaction equation

HRID 1640072 reaction equation
C(N(CC)[C:4](=[O:15])[CH2:5][C:6]1[C:11]([O:12][CH3:13])=[CH:10][CH:9]=[CH:8][C:7]=1[OH:14])C.FC(F)(F)C(O)=O.[OH-].[Na+]>C1(C)C=CC=CC=1>[CH3:13][O:12][C:11]1[C:6]2[CH2:5][C:4](=[O:15])[O:14][C:7]=2[CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 59439469HCID 59439469, compound

Product 1

HCID 45122633HCID 45122633, compoundYield 82.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
125 °C

Procedure

A solution of 0.47 g (2.0 mmol) of N,N-diethyl-(2-hydroxy-6-methoxyphenyl)acetamide in 5.0 mL of toluene was added with 0.92 mL (1.36 g, 12 mmol) of trifluoroacetic acid and heated and stirred on a 125° C. oil bath of for 71 minutes. The mixture was cooled under room temperature, and after that added with 24 mL of 0.5 N aqueous sodium hydroxide, while being stirred, and then transferred into a separatory funnel and settled. The aqueous layer was separated and discarded and after the organic layer was washed with 5 mL of water twice, the solvent was evaporated to obtain 0.27 g of the title compound.

Workup

  1. temperatureheated
  2. temperatureThe mixture was cooled under room temperature
  3. stirringwhile being stirred
  4. customtransferred into a separatory funnel
  5. customThe aqueous layer was separated
  6. washafter the organic layer was washed with 5 mL of water twice
  7. customthe solvent was evaporated

Sources & evidence

ORD record
ord-5f45675d53fd4cad9722af2984e94fc4
Source dataset
uspto-grants-2012_02
Patent number
US08110688B2

Reaction notes

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