4-Nitrobenzoic Acid → Methyl [6-(4-nitrobenzoyl)-2H-1,3-benzodioxol-5-yl]acetate

HRID 442662Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 442662
[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([CH2:10][C:11]([O:13][CH3:14])=[O:12])=[CH:4][C:3]=2[O:2]1.[N+:15]([C:18]1[CH:26]=[CH:25][C:21]([C:22](O)=[O:23])=[CH:20][CH:19]=1)([O-:17])=[O:16].O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.C([O-])([O-])=O.[K+].[K+]>C(Cl)CCl.O>[CH2:1]1[O:2][C:3]2[C:8](=[CH:7][C:6]([C:22](=[O:23])[C:21]3[CH:20]=[CH:19][C:18]([N+:15]([O-:17])=[O:16])=[CH:26][CH:25]=3)=[C:5]([CH2:10][C:11]([O:13][CH3:14])=[O:12])[CH:4]=2)[O:9]1

Komponenten

7

Edukt 4

HCID 61084-Nitrobenzoic AcidHCID 11430Potassium CarbonateHCID 14812Phosphorus oxide (P4O10)HCID 266588Methyl 2-(1,3-dioxaindan-5-yl)acetate

Produkt 1

HCID 404213Methyl [6-(4-nitrobenzoyl)-2H-1,3-benzodioxol-5-yl]acetateAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 111,2-DichloroethaneLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of methyl 3,4-methylenedioxyphenylacetate (5.4 g, 28 mmol) in ClCH2CH2Cl (100 mL) was added 4-nitrobenzoic acid (7.2 g, 43 mmol) and P2O5 (18 g) at room temperature under argon. The mixture was refluxed for 28 h, cooled to room temperature, then cold water was added slowly. The resulting mixture was carefully neutralized with solid K2CO3, and extracted with 1:1 hexane/EtOAc (2×300 mL). The combined extracts were washed with water and brine, and dried over Na2SO4. The solvent was removed in vacuo and the resulting residue was separated by chromatography (3:1 hexane/EtOAc) to afford the title compound as a yellow solid (4.7 g, 14 mmol, 50%). 1H NMR (CDCl3) 8.32 (d, 2H, J=8.5), 7.92 (d, 2H, J=8.5), 6.85 (s, 1H), 6.81 (s, 1H), 6.07 (s, 2H), 3.88 (s, 2H), 3.63 (s, 3H).

Aufarbeitung

  1. temperatureThe mixture was refluxed for 28 h
  2. extractionextracted with 1:1 hexane/EtOAc (2×300 mL)
  3. washThe combined extracts were washed with water and brine
  4. dry with materialdried over Na2SO4
  5. customThe solvent was removed in vacuo
  6. customthe resulting residue was separated by chromatography (3:1 hexane/EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-e7efa73de63944e1bb9d22e90b559737
Quelldatensatz
uspto-grants-1999_04
Patentnummer
US05891871

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