Potassium Carbonate → Ethyl 4-((3-formyl-4-nitrophenyl)oxy)butyrate

HRID 1199976Notes

Reaction equation

HRID 1199976 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([CH:9]=1)[CH:7]=[O:8].Br[CH2:14][CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:20]([O:19][C:17](=[O:18])[CH2:16][CH2:15][CH2:14][O:1][C:2]1[CH:3]=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([CH:9]=1)[CH:7]=[O:8])[CH3:21]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 392115-Hydroxy-2-nitrobenzaldehydeHCID 76300Ethyl 4-bromobutyrate

Product 1

HCID 10588876Ethyl 4-((3-formyl-4-nitrophenyl)oxy)butyrateYield 91.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a stirred solution of 5-hydroxy-2-nitrobenzaldehyde (29.8 g, 0.178 mol) and ethyl 4-bromobutyrate (26.8 ml, 0.187 mol) in DMF under nitrogen is added potassium carbonate (25.1 g, 0.182 mol). The mixture is heated to 90° C. and stirred at this temperature for 2 hr, then poured into 1500 ml ice water. The mixture is extracted with ethyl ether (5×300 ml), and the ether extracts are washed with water and dried over magnesium sulfate, filtered, and concentrated to provide 45.7 g (91%) 5-(4-ethoxy-4-oxobutoxy)-2-nitrobenzaldehyde as a yellow oil. This material is dissolved in ethanol (350 ml), and potassium hydroxide (11.3 g) in water (180 ml) is added. The mixture is stirred at room temperature for 3 hr then partially evaporated to remove the ethanol. The aqueous solution is washed with ethyl ether and then acidified with 6N HCl (50 ml). The mixture is then extracted with chloroform and the organic solution dried with magnesium sulfate, filtered, and concentrated to a volume of 100 ml. Addition of hexane precipitates a yellow solid, which is collected by filtration to provide 5-(3-carboxypropyloxy)-2-nitrobenzaldehyde, mp 112°-114° C. (37.2 g, 91%).

Workup

  1. extractionThe mixture is extracted with ethyl ether (5×300 ml)
  2. washthe ether extracts are washed with water
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b56a979b1d5d4f9499dbbaa3bf9056ce
Source dataset
uspto-grants-1990_02
Patent number
US04904667

Reaction notes

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