Water → Methyl 3-isopropoxy-4-nitrobenzoate

HRID 356971

Reaction equation

HRID 356971 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[N+:12]([O-:14])=[O:13])[C:5]([O:7][CH3:8])=[O:6].C(=O)([O-])[O-].[K+].[K+].Br[CH:22]([CH3:24])[CH3:23].O>CN(C)C=O>[CH:22]([O:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[N+:12]([O-:14])=[O:13])[C:5]([O:7][CH3:8])=[O:6])([CH3:24])[CH3:23]

Participants

6

Reactant 4

HCID 962WaterHCID 63582-BromopropaneHCID 11430Potassium CarbonateHCID 294866Methyl 3-hydroxy-4-nitrobenzoate

Product 1

HCID 21187964Methyl 3-isopropoxy-4-nitrobenzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of methyl 3-hydroxy-4-nitrobenzoate (5.9 g) in dimethylformamide (40 mL) is treated with potassium carbonate (6.2 g) and 2-bromopropane (3.7 g), and the stirred solution is heated at 60°-65° C. for 4 hours. After cooling, water (100 mL) is added and the solution is extracted with toluene (2×100 mL) The combined organic extracts are dried over magnesium sulfate and evaporated in vacuo, to give methyl 3-isopropoxy-4-nitrobenzoate, in the form of a pale yellow solid (5.9 g), m.p. 46°-48° C.

Workup

  1. temperaturethe stirred solution is heated at 60°-65° C. for 4 hours
  2. temperatureAfter cooling
  3. extractionthe solution is extracted with toluene (2×100 mL) The combined organic extracts
  4. dry with materialare dried over magnesium sulfate
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-90074f4ec8f14455b9178da867a3572d
Source dataset
uspto-grants-1998_11
Patent number
US05840724

Linked notes

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