Ethanol → HCID 11183148, compound

HRID 1720263Notes

Reaction equation

HRID 1720263 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][CH:5]=1)=[O:3].[O-:13][CH2:14]C.[Na+].C(O)C.[Na].C(OCC)=O>O1CCCC1.O>[N+:10]([C:7]1[CH:6]=[CH:5][C:4]([C:2]([CH2:1][CH:14]=[O:13])=[O:3])=[CH:9][CH:8]=1)([O-:12])=[O:11]

Participants

8

Reactant 5

HCID 702EthanolHCID 7487p-NitroacetophenoneHCID 8025Ethyl formateHCID 2723922Sodium ethoxideHCID 5360545Sodium

Product 1

HCID 11183148HCID 11183148, compoundYield 28%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-nitroacetophenone (8.26 g, 50 mmol) in anhydrous tetrahydrofuran (THF) at 0° C. was slowly added sodium ethoxide in ethanol (prepared from 1.27. g (55 mmol) sodium in 26 ml ethanol) followed by addition of ethyl formate (5.56 g, 75 mmol). The reaction was allowed to slowly warm to room temperature and stir overnight. The reaction was diluted with water (800 ml) and washed with ether. The aqueous layer was acidified (pH 1-2) with concentrated hydrochloric acid (HCl) and the mixture extracted with ethyl acetate. The combined organic layers were dried (Na2SO4) and the solvent was removed by rotary evaporation to give 4-nitrobenzoylacetaldehyde (2.69 g, 28%) as an orange solid.

Workup

  1. customat 0° C.
  2. washwashed with ether
  3. extractionthe mixture extracted with ethyl acetate
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. customthe solvent was removed by rotary evaporation

Sources & evidence

ORD record
ord-475e9f15c43a461d8ffde5d0d909615f
Source dataset
uspto-grants-1996_04
Patent number
US05506235

Reaction notes

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