2-Nitrophenol → HCID 3339760, compound

HRID 366026Notes

Reaction equation

HRID 366026 reaction equation
[C:1]1([CH:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:8]([OH:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N+:17]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1O)([O-:19])=[O:18]>N1C=CC=CC=1.CCOC(C)=O.C(O)(C)C>[C:1]1([CH:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:8]([O:10][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2[N+:17]([O-:19])=[O:18])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 2

HCID 69472-NitrophenolHCID 8333Diphenylacetic Acid

Product 1

HCID 3339760HCID 3339760, compound

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 3776IsopropanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A solution of diphenylacetic acid (30.0 g; 141 mmol) and o-nitrophenol (39.3 g; 282 mmol) in pyridine (250 mL) was cooled to 0° C. N,N1 -dicyclohexylcarbodiimide (27.6 g; 134 mmol) was added at 0° C. The solution was stirred at 0° C. for several hours, warmed to room temperature and stirred overnight. The resulting heterogeneous solution was diluted with EtOAc and filtered. The filtrate was concentrated to afford a thick oil which was dissolved in a minimal amount of warm isopropanol. Upon cooling the sub-title compound began to crystallize from solution. The crystals were collected and dried under vacuum to afford the sub-title compound (37.3 g; 82%) as an off-white powder.

Workup

  1. temperaturewarmed to room temperature
  2. stirringstirred overnight
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated
  5. customto afford a thick oil which

Sources & evidence

ORD record
ord-ffb1d2a3ff08419e8c44274c702d226b
Source dataset
uspto-grants-2000_10
Patent number
US06127414

Reaction notes

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