Ethanol → Ethyl 5-phenylsalicylate

HRID 2086523

Reaktionsgleichung

Reaktionsgleichung von HRID 2086523
[C:1]1([C:7]2[CH:15]=[C:11]([C:12]([OH:14])=[O:13])[C:10]([OH:16])=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:17](O)[CH3:18].S(=O)(=O)(O)O.Cl.C(OCC)(=O)C>C1(C)C=CC=CC=1>[C:1]1([C:7]2[CH:15]=[C:11]([C:12]([O:14][CH2:17][CH3:18])=[O:13])[C:10]([OH:16])=[CH:9][CH:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Komponenten

6

Edukt 4

HCID 702EthanolHCID 1118Sulfuric AcidHCID 675844-Hydroxy[1,1'-biphenyl]-3-carboxylic acidHCID 21866389Hydrogen chloride-ethyl acetate

Produkt 1

HCID 12265001Ethyl 5-phenylsalicylateAusbeute 55 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

To 18.58 g of 5-phenylsalicylic acid, 350 ml of ethanol, 100 ml of toluene and 42 ml of concentrated sulfuric acid were added. The mixture was heated under reflux for 14 hours. After it was confirmed with TLC that the starting materials were almost disappeared, the reaction liquid was poured into a mixed medium of diluted hydrochloric acid-ethyl acetate. The mixture was extracted, and the organic phase was collected and washed with saturated sodium chloride aqueous solution. After dried with magnesium sulfate, the liquid was concentrated to form a crude product. The product was recrystallized from ethanol to obtain 11.53 g of ethyl 5-phenylsalicylate in the form of colorless crystallites. The yield was 55%. The product was confirmed with NMR and mass spectroscopy.

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 14 hours
  3. customthe reaction liquid
  4. extractionThe mixture was extracted
  5. customthe organic phase was collected
  6. washwashed with saturated sodium chloride aqueous solution
  7. dry with materialAfter dried with magnesium sulfate
  8. concentrationthe liquid was concentrated
  9. customto form a crude product
  10. customThe product was recrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-2a0a7cb5667b4c96b95dee350782476e
Quelldatensatz
uspto-grants-2004_04
Patentnummer
US06726966B2

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