Potassium Carbonate → 4-(Methoxycarbonylmethoxy)-3-nitrophenyl Benzoate

HRID 1295577Notes

Reaction equation

HRID 1295577 reaction equation
[C:1]([O:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[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]([O:16][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:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

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

Product 1

HCID 694126724-(Methoxycarbonylmethoxy)-3-nitrophenyl BenzoateYield 61%

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 mol), 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 following decolourisation with charcoal 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 following decolourisation with charcoal

Sources & evidence

ORD record
ord-80640505586f49a9ad9c138e8096f372
Source dataset
uspto-grants-2007_07
Patent number
US07244726B2

Reaction notes

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