Ethanol → HCID 12832890, compound

HRID 2286125Notes

Reaction equation

HRID 2286125 reaction equation
[H-].[Na+].[C:3]([O:10][CH2:11][CH3:12])(=[O:9])[C:4]([O:6]CC)=O.C(O)C.[CH3:16][C:17]([C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[C:20]=1[Cl:26])=[O:18]>C(O)(=O)C.O.CCOCC>[Cl:26][C:20]1[C:21]([Cl:25])=[CH:22][CH:23]=[CH:24][C:19]=1[C:17](=[O:18])[CH2:16][C:4](=[O:6])[C:3]([O:10][CH2:11][CH3:12])=[O:9]

Participants

8

Reactant 4

HCID 702EthanolHCID 7268Diethyl OxalateHCID 24758Sodium hydrideHCID 919861-(2,3-Dichlorophenyl)ethan-1-one

Product 1

HCID 12832890HCID 12832890, compoundYield 34.4%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

To 14 g of sodium hydride (50%) were added dropwise 21.3 g of diethyl oxalate, 0.54 ml of ethanol and then 160 ml of ether solution containing 30 g of 2,3-dichloroacetophenone with stirring under cooling with ice. The reaction was carried out under the state free from water. The reaction was continued at room temperature for 40 minutes with stirring after the dropping and further carried out for 45 minutes under reflux. The reaction mixture was poured into ice-cold water containing 17.5 g of acetic acid and after stirring the mixture was filtered. The organic layer was separated, dehydrated and concentrated. The residue was recrystallized from n-hexane to obtain 14.5 g of ethyl 4-(2,3-dichlorophenyl)-2,4-dioxobutyrate (white needles, m.p. 57°-58° C.).

Workup

  1. temperatureunder cooling with ice
  2. stirringwith stirring after the dropping
  3. waitfurther carried out for 45 minutes
  4. temperatureunder reflux
  5. stirringafter stirring the mixture
  6. filtrationwas filtered
  7. customThe organic layer was separated
  8. concentrationconcentrated
  9. customThe residue was recrystallized from n-hexane

Sources & evidence

ORD record
ord-efc0a605937e42e28324492bd234ace1
Source dataset
uspto-grants-1982_04
Patent number
US04326881

Reaction notes

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