Hydrochloric Acid → Dimethyl 2-[(4-nitrophenyl)methyl]propanedioate

HRID 1256874Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1256874
[C:1]([O:8][CH3:9])(=[O:7])[CH2:2][C:3]([O:5][CH3:6])=[O:4].[H-].[Na+].[N+:12]([C:15]1[CH:22]=[CH:21][C:18]([CH2:19]Br)=[CH:17][CH:16]=1)([O-:14])=[O:13].Cl>C1COCC1>[CH3:6][O:5][C:3](=[O:4])[CH:2]([CH2:19][C:18]1[CH:21]=[CH:22][C:15]([N+:12]([O-:14])=[O:13])=[CH:16][CH:17]=1)[C:1]([O:8][CH3:9])=[O:7]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 7943Dimethyl malonateHCID 24758Sodium hydrideHCID 660114-Nitrobenzyl bromide

Produkt 1

HCID 4156732Dimethyl 2-[(4-nitrophenyl)methyl]propanedioateAusbeute 68,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of dimethyl malonate (5.53 g) in THF (100 mL) was added 60% sodium hydride (1.84 g) under ice-cooling, and the mixture was stirred for 30 min. 4-Nitrobenzyl bromide (9.04 g) was added to this mixture under ice-cooling, and the mixture was allowed to warm to room temperature while stirring for 4 hr. The reaction mixture was adjusted to pH=2-3 by the addition of dilute hydrochloric acid, the precipitate was removed by filtration, and the filtrate was extracted with ethyl acetate (200 mL). The organic layer was washed with saturated brine and concentrated under reduced pressure to give the title compound (7.66 g) as a pale-yellow solid.

Aufarbeitung

  1. temperaturecooling
  2. temperaturecooling
  3. stirringwhile stirring for 4 hr
  4. customthe precipitate was removed by filtration
  5. extractionthe filtrate was extracted with ethyl acetate (200 mL)
  6. washThe organic layer was washed with saturated brine
  7. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-59f642fac24c4ff2a3804cfb1e66fd79
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08461209B2

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