Water → Methyl 3-isopropoxy-4-nitrobenzoate

HRID 1870420Notes

Reaction equation

HRID 1870420 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

Conditions

Temperature
62.5 °C

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. temperatureAfter cooling
  2. extractionthe solution is extracted with toluene (2×100 mL) The combined organic extracts
  3. dry with materialare dried over magnesium sulfate
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-d1fd7ef4b7b44ff78e3386d2984d66bd
Source dataset
uspto-grants-2000_08
Patent number
US06096768

Reaction notes

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