Dimethyl malonate → Methyl 2-hydroxy-4-oxo-6-pentylcyclohex-2-ene-1-carboxylate

HRID 2201166

Reaktionsgleichung

Reaktionsgleichung von HRID 2201166
C[O-].[Na+].[C:4]([O:11][CH3:12])(=[O:10])[CH2:5][C:6]([O:8]C)=O.[CH3:13][C:14](=[O:22])[CH:15]=[CH:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]>CO>[CH2:17]([CH:16]1[CH:5]([C:4]([O:11][CH3:12])=[O:10])[C:6]([OH:8])=[CH:13][C:14](=[O:22])[CH2:15]1)[CH2:18][CH2:19][CH2:20][CH3:21]

Komponenten

5

Edukt 3

HCID 7943Dimethyl malonateHCID 26630Non-3-en-2-oneHCID 10942334Sodium Methoxide

Produkt 1

HCID 2785071Methyl 2-hydroxy-4-oxo-6-pentylcyclohex-2-ene-1-carboxylateAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a stirring solution of sodium methoxide (32.4 g, 0.60 mol) and dimethyl malonate (90 g, 0.68 mol) in 230 mL of anhydrous methanol was added portion wise 75 g (0.48 mol) of 90% 3-nonen-2-one. The reaction mixture was then refluxed for 3 h under N2 and allowed to cool to room temperature. The solvent was distilled under reduced pressure and the residue dissolved in 350 mL of water. The slurry of white crystals and the almost clear solution was extracted thrice with 80 mL of chloroform. The aqueous layer was acidified to pH 4 with concentrated HCl and the white precipitate that formed was allowed to stand overnight prior to filtration. The crystals were dried at 50° C. under high vacuum for 5 hours to yield 106.5 g (0.4416 mol) (92%) of methyl 6-n-Pentyl-2-hydroxy-4-oxo-cyclohex-2-ene-1-carboxylate (mp 96-98 C). The product was recrystallized using a mixture of petroleum ether:ethyl acetate (9:1), and gave 94 g of pure methyl 6-n-Pentyl-2-hydroxy-4-oxo-cyclohex-2-ene-1-carboxylate (melting point of 98-100 C).

Aufarbeitung

  1. temperatureThe reaction mixture was then refluxed for 3 h under N2
  2. distillationThe solvent was distilled under reduced pressure
  3. dissolutionthe residue dissolved in 350 mL of water
  4. extractionThe slurry of white crystals and the almost clear solution was extracted thrice with 80 mL of chloroform
  5. customthe white precipitate that formed
  6. filtrationto filtration
  7. customThe crystals were dried at 50° C. under high vacuum for 5 hours

Quellen und Nachweise

ORD-Eintrag
ord-d8da0fb240ff4ba7b791d79607b5acbd
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09359625B2

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