Hydrochloric Acid → Ethyl 2-(4-nitrophenyl)butanoate

HRID 1156820Notes

Reaction equation

HRID 1156820 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:6][CH:5]=1)([O-:3])=[O:2].[H-].[Na+].[CH2:18](I)[CH3:19].Cl>O.C1(C)C=CC=CC=1.CN(C)C=O>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH:10]([CH2:18][CH3:19])[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 6340IodoethaneHCID 24758Sodium hydrideHCID 79517Ethyl 4-nitrophenylacetate

Product 1

HCID 237528Ethyl 2-(4-nitrophenyl)butanoate

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Procedure

The starting material is prepared as follows: To the mixture of 104 g ethyl 4-nitrophenyl-acetate, 350 ml dimethylformamide and 350 ml toluene, 19 g 50% sodium hydride in mineral oil are added during 3/4 hour at 10° while stirring. After 11/2 hours, 78 g ethyl iodide are added during 1 hour while stirring. After 11/2 hours, some water is added dropwise and the mixture acidified with 10% hydrochloric acid. The mixture is extracted with diethyl ether, the extract dried and evaporated, to yield the ethyl α-(4-nitrophenyl)-butyrate.

Workup

  1. customThe starting material is prepared
  2. additionare added during 3/4 hour at 10°
  3. stirringwhile stirring
  4. extractionThe mixture is extracted with diethyl ether
  5. customthe extract dried
  6. customevaporated

Sources & evidence

ORD record
ord-38ef95ca5fa54a3ea28ba30cde454dc3
Source dataset
uspto-grants-1982_06
Patent number
US04337264

Reaction notes

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