Hydrochloric Acid → HCID 54028213, compound

HRID 1155715Notes

Reaction equation

HRID 1155715 reaction equation
[H-].[Na+].[N+:3]([C:6]1[CH:16]=[CH:15][C:9]([CH:10]=[CH:11][C:12](=[O:14])[CH3:13])=[CH:8][CH:7]=1)([O-:5])=[O:4].[C:17](OCC)(=[O:23])[C:18]([O:20][CH2:21][CH3:22])=[O:19].Cl>CCOCC.O1CCCC1.C(O)C>[N+:3]([C:6]1[CH:7]=[CH:8][C:9]([CH:10]=[CH:11][C:12](=[O:14])[CH2:13][C:17](=[O:23])[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:15][CH:16]=1)([O-:5])=[O:4]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 7268Diethyl OxalateHCID 24758Sodium hydrideHCID 1019243490-37-7

Product 1

HCID 54028213HCID 54028213, compoundYield 44.3%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ethanol (9.5 ml) is added to a suspension of 60% sodium hydride (26.3 g) in anhydrous ether (750 ml), and thereto is added dropwise a mixture of p-nitrobenzalacetone (130 g), diethyl oxalate (99.4 g) and anhydrous tetrahydrofuran (550 ml) at 5°-10° C. with agitation. The mixture is agitated at room temperature for one hour, and thereto is added 10% hydrochloric acid (350 ml). The precipitated yellow solid is collected by filtration, washed with ether and then recrystallized from acetone to give ethyl 6-(4-nitrophenyl)-2,4-dioxo-hex-5-enoate (87.8 g). M.P. 148.5°-153.5° C.

Workup

  1. additionis added dropwise
  2. filtrationThe precipitated yellow solid is collected by filtration
  3. washwashed with ether
  4. customrecrystallized from acetone

Sources & evidence

ORD record
ord-56006cb5cd864212a21e8b5f3aae5bbc
Source dataset
uspto-grants-1982_06
Patent number
US04332809

Reaction notes

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