Ethyl Acetate → 3,4-Dihydro-7-hydroxy-4-(1-naphthyl)coumarin

HRID 224927

Reaktionsgleichung

Reaktionsgleichung von HRID 224927
[C:1]1([CH:11]=[CH:12][C:13]([OH:15])=[O:14])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.C([O:19][CH2:20][CH3:21])(=O)C>Cl>[OH:19][C:20]1[CH:21]=[C:3]2[C:2]([CH:11]([C:1]3[C:10]4[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=4)[CH:4]=[CH:3][CH:2]=3)[CH2:12][C:13](=[O:15])[O:14]2)=[CH:1][CH:10]=1

Komponenten

4

Edukt 2

HCID 8857Ethyl AcetateHCID 983073-(1-Naphthalenyl)-2-propenoic acid

Produkt 1

HCID 205705223,4-Dihydro-7-hydroxy-4-(1-naphthyl)coumarin

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 313Hydrochloric AcidLösungsmittel2×

Versuchsvorschrift

A mixture of 3-(1-naphthyl)acrylic acid (50.0 g., 0.25 moles) in concentrated hydrochloric acid (1500 ml.) was stirred at reflux while a vigorous stream of hydrogen chloride was passed through the reaction for 6 hours. The solution was allowed to stand overnight at room temperature, then filtered to give a white solid which was dissolved in ethyl acetate and washed with saturated sodium bicarbonate solution (3×). The ethyl acetate solution was dried and removal of solvent gave the dihydrocoumarin as a white solid (43.5 g., 85% based on consumed starting material) m.p. 193°-196° C.

Aufarbeitung

  1. customwas passed through the reaction for 6 hours
  2. filtrationfiltered
  3. customto give a white solid which
  4. washwashed with saturated sodium bicarbonate solution (3×)
  5. dry with materialThe ethyl acetate solution was dried
  6. customremoval of solvent
  7. customgave
  8. customthe dihydrocoumarin as a white solid (43.5 g., 85% based on consumed starting material) m.p. 193°-196° C.

Quellen und Nachweise

ORD-Eintrag
ord-a6a25606323d4c939bd4dc5b66e88a2f
Quelldatensatz
uspto-grants-1980_11
Patentnummer
US04234726

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