Hydrochloric Acid → 2-acetoxy-4-{(2E)-3,7-dimethylocta-2,6-dienyloxy}benzoic acid

HRID 264359Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 264359
[CH3:1]/[C:2](/[CH2:16][CH2:17][CH:18]=[C:19]([CH3:21])[CH3:20])=[CH:3]\[CH2:4][O:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([OH:12])=[O:11])=[C:8]([OH:15])[CH:7]=1.[C:22](OC(=O)C)(=[O:24])[CH3:23].Cl>N1C=CC=CC=1>[C:22]([O:15][C:8]1[CH:7]=[C:6]([O:5][CH2:4]/[CH:3]=[C:2](\[CH3:1])/[CH2:16][CH2:17][CH:18]=[C:19]([CH3:21])[CH3:20])[CH:14]=[CH:13][C:9]=1[C:10]([OH:12])=[O:11])(=[O:24])[CH3:23]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 104243134-{(2E)-3,7-dimethylocta-2,6-dienyloxy}-2-hydroxybenzoic acid

Produkt 1

HCID 691303622-acetoxy-4-{(2E)-3,7-dimethylocta-2,6-dienyloxy}benzoic acidAusbeute 48 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

To 10 ml of a pyridine solution containing 0.82 g (2.82 mmol) of 4-{(2E)-3,7-dimethylocta-2,6-dienyloxy}-2-hydroxybenzoic acid was added 0.72 g (7.1 mmol) of acetic anhydride, followed by stirring at room temperature for 1 hour. The reaction mixture was poured into a 2% hydrochloric acid aqueous solution and extracted with ethyl acetate. The organic layer was washed successively with water and a saturated sodium chloride aqueous solution, dried over sodium sulfate, and concentrated. The resulting crude product was recrystallized from an ethyl ether/hexane mixed solvent to obtain 0.45 g (yield: 48%) of 2-acetoxy-4-{(2E)-3,7-dimethylocta-2,6-dienyloxy}benzoic acid represented by the following structural formula (hereinafter referred to as compound 45) as white crystals. The analytical results are shown below. ##STR66##

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed successively with water
  3. dry with materiala saturated sodium chloride aqueous solution, dried over sodium sulfate
  4. concentrationconcentrated
  5. customThe resulting crude product was recrystallized from an ethyl ether/hexane mixed solvent

Quellen und Nachweise

ORD-Eintrag
ord-169ba451713944ffb01cacfa03df35c5
Quelldatensatz
uspto-grants-1997_07
Patentnummer
US05646184

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