Phenol → HCID 12196105, compound

HRID 1581680Notes

Reaction equation

HRID 1581680 reaction equation
Cl[C:2]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[C:14]1([OH:20])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C[O-].[Na+]>CO>[O:20]([C:2]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 996PhenolHCID 74482-Chloro-4-nitrobenzoic acidHCID 10942334Sodium Methoxide

Product 1

HCID 12196105HCID 12196105, compoundYield 120.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
180 °C

Procedure

To a stirred solution of 2-chloro-4-nitrobenzoic acid (3 g, 14.9 mmole) and phenol (3 g, 31.9 mmole) in MeOH (20 mL) was added a solution of NaOMe in MeOH (25 wt %, 9 mL, 39.4 mmole). After 15 minutes the solution was concentrated to dryness and the residue was taken up in dimethylacetamide (50 mL). Copper powder (100 mg) was added and the mixture was heated at reflux with stirring (180° C. oil bath). After 1 hr the reaction was cooled to RT, acidified with 1.0 N HCl (40 mL), and extracted with EtOAc. The combined organic layers were washed with brine, dried (MgSO4), and concentrated under vacuum. The remaining residue was triturated with 1:1 Et2O/petroleum ether and dried under vacuum to afford the title compound (4.65 g). This was used without further purification.

Workup

  1. concentrationAfter 15 minutes the solution was concentrated to dryness
  2. additionCopper powder (100 mg) was added
  3. temperaturethe mixture was heated
  4. temperatureat reflux
  5. temperatureAfter 1 hr the reaction was cooled to RT
  6. extractionextracted with EtOAc
  7. washThe combined organic layers were washed with brine
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated under vacuum
  10. customThe remaining residue was triturated with 1:1 Et2O/petroleum ether
  11. customdried under vacuum

Sources & evidence

ORD record
ord-78080c5f44864728903e2b1345b5c5a5
Source dataset
uspto-grants-2004_05
Patent number
US06730684B1

Reaction notes

Loading…