Tetrahydrophthalic anhydride, cis- → 6-(3,4-Dimethoxy-benzoyl)-cyclohex-3-enecarboxylic acid

HRID 1919523Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1919523
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([Mg]Br)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[C:13]1(=[O:23])[O:18][C:16](=[O:17])[C@H:15]2[CH2:19][CH:20]=[CH:21][CH2:22][C@@H:14]12>C1COCC1.C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:6]=[CH:7][C:8]=1[O:9][CH3:10])[C:13]([CH:14]1[CH:15]([C:16]([OH:18])=[O:17])[CH2:19][CH:20]=[CH:21][CH2:22]1)=[O:23]

Komponenten

5

Edukt 2

HCID 98495Tetrahydrophthalic anhydride, cis-HCID 178491916HCID 178491916, Verbindung

Produkt 1

HCID 222196226-(3,4-Dimethoxy-benzoyl)-cyclohex-3-enecarboxylic acidAusbeute 10 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of 3,4-dimethoxyphenylmagnesium bromide (59 mmol, 0.29 M) in THF was added dropwise to an ice-cooled solution of cis-1,2,3,6-tetrahydrophthalic anhydride in THF (120 mL) over a 1 h period. After the addition was complete, the resulting mixture was stirred for another 30 min at 0° C. The reaction mixture was allowed to warn to room temperature overnight. The reaction was quenched with sat. NH4Cl(aq) and then the pH was adjusted to 2 with concentrated HCl(aq) and extracted with diethyl ether. The combined organic extracts were washed with water and subsequently extracted with 1 M NaOH(aq). The combined aqueous extracts were neutralized with conc. HCl(aq) and extracted with EtOAc. The combined organic extracts were dried over MgSO4, filtered through paper, and concentrated under reduced pressure to give an oil. The oil was dissolved in CH2Cl2 and filtered through silica to remove any dicarboxylic acid formed during the reaction work up. The product was recrystallized in diethyl ether to afford a white solid (1.62 g, 5.58 mmol, 10%).

Aufarbeitung

  1. additionAfter the addition
  2. waitto warn to room temperature overnight
  3. customThe reaction was quenched with sat. NH4Cl(aq)
  4. extractionextracted with diethyl ether
  5. washThe combined organic extracts were washed with water
  6. extractionsubsequently extracted with 1 M NaOH(aq)
  7. extractionextracted with EtOAc
  8. dry with materialThe combined organic extracts were dried over MgSO4
  9. filtrationfiltered through paper
  10. concentrationconcentrated under reduced pressure
  11. customto give an oil
  12. filtrationfiltered through silica
  13. customto remove any dicarboxylic acid
  14. customformed during the reaction work up
  15. customThe product was recrystallized in diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-0239bc3793164dcba7e3278ee7e5321f
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08168635B2

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