Phenol → Methyl 2-methyl-5-nitro-4-phenylbenzoate

HRID 1106499Notes

Reaction equation

HRID 1106499 reaction equation
Br[C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([CH3:15])[CH:3]=1.C([O-])([O-])=O.[K+].[K+].[C:22]1(O)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CN(C=O)C>[CH3:15][C:4]1[CH:3]=[C:2]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7]

Participants

5

Reactant 3

HCID 996PhenolHCID 11430Potassium CarbonateHCID 18788736HCID 18788736, compound

Product 1

HCID 18788795Methyl 2-methyl-5-nitro-4-phenylbenzoateYield 58.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

22.6 g of methyl 4-bromo-2-methyl-5-nitrobenzoate, 23 g of K2CO3 and 7.8 g of phenol were stirred at 120° C. for 2 hours in 300 ml of DMF. The solvent was removed in vacuo, 2 l of water were added, and the mixture was adjusted to pH=7 using aqueous HCl solution and extracted 3 times using 500 ml of EA each time. The organic phase was dried over Na2SO4, the solvent was removed in vacuo and chromatography on silica gel using EA/HEP 1:4 yielded 13 g of a colorless oil.

Workup

  1. customThe solvent was removed in vacuo, 2 l of water
  2. additionwere added
  3. extractionextracted 3 times
  4. dry with materialThe organic phase was dried over Na2SO4
  5. customthe solvent was removed in vacuo and chromatography on silica gel

Sources & evidence

ORD record
ord-95afd47624a94617992618b2d30f490c
Source dataset
uspto-grants-2000_05
Patent number
US06057322

Reaction notes

Loading…