Sodium hydride → 4-[2-(1,2,3,4-Tetramethoxy-6,7,8,9-tetrahydro-5H-benzo[a]cyclohepten-7-yl)ethoxy]benzoic acid

HRID 2268497Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2268497
[CH3:1][O:2][C:3]1[C:8]2[CH2:9][CH2:10][CH:11]([CH2:14][CH2:15][O:16][C:17]3[CH:27]=[CH:26][C:20]([C:21]([O:23]CC)=[O:22])=[CH:19][CH:18]=3)[CH2:12][CH2:13][C:7]=2[C:6]([O:28][CH3:29])=[C:5]([O:30][CH3:31])[C:4]=1[O:32][CH3:33].[H-].[Na+]>CO>[CH3:1][O:2][C:3]1[C:8]2[CH2:9][CH2:10][CH:11]([CH2:14][CH2:15][O:16][C:17]3[CH:18]=[CH:19][C:20]([C:21]([OH:23])=[O:22])=[CH:26][CH:27]=3)[CH2:12][CH2:13][C:7]=2[C:6]([O:28][CH3:29])=[C:5]([O:30][CH3:31])[C:4]=1[O:32][CH3:33]

Komponenten

4

Edukt 2

HCID 24758Sodium hydrideHCID 18348644Ethyl 4-[2-(1,2,3,4-Tetramethoxy-6,7,8,9-tetrahydro-5H-benzo[a]cyclohepten-7-yl)ethoxy]benzoate

Produkt 1

HCID 183486524-[2-(1,2,3,4-Tetramethoxy-6,7,8,9-tetrahydro-5H-benzo[a]cyclohepten-7-yl)ethoxy]benzoic acidAusbeute 80,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

The mixture of ethyl 4-[2-(1,2,3,4-tetramethoxy-6,7,8,9-tetrahydro-5H-benzo[a]cyclohepten-7-yl)ethoxy]benzoate (1.77 g), aqueous sodium hydride (3N, 1.93 ml), and methanol (30 ml) was heated under reflux for 6 hr. The reaction mixture was concentrated in vacuo, diluted with water, made acidic with hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed with water and saturated aqueous sodium chloride and dried. The solvent was removed in vacuo. The residue was recrystallized from THF-diisopropylether to yield the entitled compound (1.34 g) as crystals.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux for 6 hr
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. additiondiluted with water
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with water and saturated aqueous sodium chloride
  7. customdried
  8. customThe solvent was removed in vacuo
  9. customThe residue was recrystallized from THF-diisopropylether

Quellen und Nachweise

ORD-Eintrag
ord-7125c719bbb442bab22b22a6989c0267
Quelldatensatz
uspto-grants-2001_12
Patentnummer
US06326369B1

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