Potassium Carbonate → 4-Methoxycarbonylmethyl-3-nitrophenyl Benzoate

HRID 495419Notes

Reaction equation

HRID 495419 reaction equation
[C:1]([O:9][C:10]1[CH:15]=[CH:14][C:13](O)=[C:12]([N+:17]([O-:19])=[O:18])[CH:11]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:21][C:22]([O:24][CH3:25])=[O:23].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[C:1]([O:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:21][C:22]([O:24][CH3:25])=[O:23])=[C:12]([N+:17]([O-:19])=[O:18])[CH:11]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 11097269HCID 11097269, compound

Product 1

HCID 693569234-Methoxycarbonylmethyl-3-nitrophenyl BenzoateYield 63,436.199%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 4-hydroxy-3-nitrophenyl benzoate (48.8 g, 0.19 mol), methyl bromoacetate (28.8 g, 0.19 mmol), anhydrous potassium carbonate (33.8 g, 0.24 mol) and acetone (700 mL) was heated at reflux for 24 h. The mixture was evaporated in vacuo and the residue partitioned between aqueous NaOH (1 M, 1 L) and dichloromethane (3×200 mL). The combined organic extracts were washed with aqueous NaOH (1 M, 500 mL), water (500 mL) and brine (250 mL), then dried (Na2SO4) and evaporated in vacuo to give a solid. Crystallisation from methanol with charcoal treatment gave the title compound (38 g, 61%) as pale yellow needles.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 24 h
  3. customThe mixture was evaporated in vacuo
  4. customthe residue partitioned between aqueous NaOH (1 M, 1 L) and dichloromethane (3×200 mL)
  5. washThe combined organic extracts were washed with aqueous NaOH (1 M, 500 mL), water (500 mL) and brine (250 mL)
  6. dry with materialdried (Na2SO4)
  7. customevaporated in vacuo
  8. customto give a solid
  9. customCrystallisation from methanol with charcoal treatment

Sources & evidence

ORD record
ord-2bf46dbfaf1b4aa18235d9e9940b8f0f
Source dataset
uspto-grants-2005_09
Patent number
US06939871B2

Reaction notes

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