Dimethylformamide → HCID 69130305, Verbindung

HRID 264356

Reaktionsgleichung

Reaktionsgleichung von HRID 264356
CN(C=O)C.[OH:6][C:7]1[CH:16]=[C:15]([OH:17])[CH:14]=[CH:13][C:8]=1[C:9]([O:11][CH3:12])=[O:10].C(=O)([O-])[O-].[K+].[K+].[CH2:24](Br)/[CH:25]=[C:26](/[CH2:28][CH2:29][CH:30]=[C:31]([CH3:33])[CH3:32])\[CH3:27]>O>[CH3:27]/[C:26](/[CH2:28][CH2:29][CH:30]=[C:31]([CH3:33])[CH3:32])=[CH:25]\[CH2:24][O:17][C:15]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[C:7]([OH:6])[CH:16]=1

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 16523Methyl 2,4-DihydroxybenzoateHCID 53658672,6-Octadiene, 1-bromo-3,7-dimethyl-, (2E)-

Produkt 1

HCID 69130305HCID 69130305, VerbindungAusbeute 76,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

In 80 m of DMF were poured 13.1 g (78.0 mmol) of methyl 2,4-dihydroxybenzoate and 18.9 g (86.9 mmol) of potassium carbonate, and 12.0 g (86.9 mmol) of geranyl bromide was added thereto dropwise at 5° C. After the addition, the mixture was stirred at room temperature for 1 hour, poured into 300 ml of water, and extracted with 250 ml of ethyl acetate. The extract was washed with water and a saturated sodium chloride aqueous solution, dried over sodium sulfate, and concentrated. The resulting crude product was purified by column chromatography to obtain 18.1 g (yield: 75%) of methyl 4-{(2E)-3,7-dimethylocta-2,6-dienyloxy}-2-hydroxybenzoate represented by the following chemical formula (hereinafter referred to as compound 31) as a colorless, clear and oily substance. The analytical results are shown below. ##STR52##

Aufarbeitung

  1. additionwas added
  2. customdropwise at 5° C
  3. additionAfter the addition
  4. extractionextracted with 250 ml of ethyl acetate
  5. washThe extract was washed with water
  6. dry with materiala saturated sodium chloride aqueous solution, dried over sodium sulfate
  7. concentrationconcentrated
  8. customThe resulting crude product was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-ed26f7e8ce11468380f41976500fe5b4
Quelldatensatz
uspto-grants-1997_07
Patentnummer
US05646184

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