Benzoyl chloride → 4-Benzoyloxy-2-methylnaphthol

HRID 277629

Reaktionsgleichung

Reaktionsgleichung von HRID 277629
[CH3:1][C:2]1[CH:11]=[C:10]([OH:12])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]=1[OH:13].[C:14](Cl)(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>N1C=CC=CC=1>[C:14]([O:12][C:10]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([OH:13])=[C:2]([CH3:1])[CH:11]=1)(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Komponenten

4

Edukt 2

HCID 7412Benzoyl chlorideHCID 10209Menadiol

Produkt 1

HCID 226254094-Benzoyloxy-2-methylnaphtholAusbeute 69,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

9.7 g (0.056 mol) of 2-methyl-1,4-dihydroxynaphthalene was dissolved in 60 ml of pyridine, and, while stirring under ice-cooling, 8.4 g (0.06 mol) of benzoyl chloride was added dropwise. Following completion of the addition, stirring was continued under ice-cooling for 30 minutes, and for further one hour at room temperature. The reaction mixture was concentrated under reduced pressure, the residual oil extracted with ethyl acetate, washed with 1N HCl and then water, and the organic layer concentrated under reduced pressure. Methanol was added to the residue, the precipitated crystals collected by filtration and recrystallized from methanol to give 10.8 g of white crystals, m.p. 172-174° C.

Aufarbeitung

  1. temperaturecooling
  2. additioncompletion of the addition
  3. stirringstirring
  4. temperaturecooling for 30 minutes
  5. concentrationThe reaction mixture was concentrated under reduced pressure
  6. extractionthe residual oil extracted with ethyl acetate
  7. washwashed with 1N HCl
  8. concentrationwater, and the organic layer concentrated under reduced pressure
  9. additionMethanol was added to the residue
  10. filtrationthe precipitated crystals collected by filtration
  11. customrecrystallized from methanol

Quellen und Nachweise

ORD-Eintrag
ord-91770afe4a5f4c058ae10ae9f130275c
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06358515B2

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