Epichlorohydrin → 4-Benzyloxy-7-(2,3-epoxypropyloxy)coumarin

HRID 444214Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 444214
[CH2:1]([O:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([OH:19])=[CH:16][CH:17]=2)[O:12][C:11](=[O:20])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+].[CH2:23]([CH:25]1[O:27][CH2:26]1)Cl>C(O)C.O>[CH2:1]([O:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([O:19][CH2:23][CH:25]3[O:27][CH2:26]3)=[CH:16][CH:17]=2)[O:12][C:11](=[O:20])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

6

Edukt 3

HCID 7835EpichlorohydrinHCID 14797Potassium HydroxideHCID 134084074-Benzyloxy-7-hydroxycoumarin

Produkt 1

HCID 134084084-Benzyloxy-7-(2,3-epoxypropyloxy)coumarin

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

4-Benzyloxy-7-hydroxycoumarin (10.7 g, 0.041 mole) was dissolved in ethanol (200 ml) and a solution of potassium hydroxide (2.5 g) in water (10 ml) was added. Epichlorhydrin (40 ml) was added and the stirred mixture heated to reflux for 21/2 hr. After cooling, the solvent was removed in vacuo and the residue partitioned between water and ethyl acetate. Evaporation of the dried (MgSO4) organic phase gave the product as a white crystalline solid. Recrystallization from ethanol gave 11.1 g (83%) of material of m.p. 128°-129° C.; (Found; C, 70.48; H, 4.92; C19H16O5 requires; C, 70.36; H, 4.97%).

Aufarbeitung

  1. temperaturethe stirred mixture heated
  2. temperatureto reflux for 21/2 hr
  3. temperatureAfter cooling
  4. customthe solvent was removed in vacuo
  5. customthe residue partitioned between water and ethyl acetate
  6. customEvaporation of the
  7. dry with materialdried (MgSO4) organic phase

Quellen und Nachweise

ORD-Eintrag
ord-9d0ac0a5027940a7aa31852e5a9d8c75
Quelldatensatz
uspto-grants-1981_04
Patentnummer
US04263299

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