Acetic Acid → HCID 15480995, compound

HRID 1634323Notes

Reaction equation

HRID 1634323 reaction equation
Cl[C:2]1[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][C:3]=1[CH:4]=[O:5].[C:14]1([OH:20])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C([O-])([O-])=O.[K+].[K+].C(O)(=O)C>CN(C=O)C>[O:20]([C:2]1[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][C:3]=1[CH:4]=[O:5])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 996PhenolHCID 11430Potassium CarbonateHCID 6881812-Chloro-5-(trifluoromethyl)benzaldehyde

Product 1

HCID 15480995HCID 15480995, compoundYield 72.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 2-chloro-5-(trifluoromethyl)benzaldehyde (500 mg, 2.40 mmol) in DMF (5 ml) was added phenol (226 mg, 2.40 mmol), K2CO3 (663 mg, 4.79 mmol). The reaction suspension was stirred at room temperature for 1 hr, then at 80° C. for 1.5 hr. The reaction mixture was neutralizing for acetic acid (0.5 ml), the solvent was removed. To the solid residue was added water and the mixture was extracted with CH2Cl2. The combined CH2Cl2 extracts were washed with sat. NaHCO3 aq., dried with MgSO4, and concentrated to give crude Compound 6 as a yellow oil. This was purified with chromatography to give pure Compound 6 as a yellow oil (466 mg, 72.9%).

Workup

  1. waitat 80° C. for 1.5 hr
  2. customthe solvent was removed
  3. additionTo the solid residue was added water
  4. extractionthe mixture was extracted with CH2Cl2
  5. washThe combined CH2Cl2 extracts were washed with sat. NaHCO3 aq.
  6. dry with materialdried with MgSO4
  7. concentrationconcentrated
  8. customto give crude Compound 6 as a yellow oil
  9. customThis was purified with chromatography

Sources & evidence

ORD record
ord-3011b0b897164dc1b4e22cb97645ab35
Source dataset
uspto-grants-2003_01
Patent number
US06506775B1

Reaction notes

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