Epichlorohydrin → 1,2,3,4-Tetrahydro-5-[2,3-epoxy-propoxy]-2-naphthol

HRID 263320Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 263320
[C:1]1([OH:12])[C:10]2[CH2:9][CH2:8][CH:7]([OH:11])[CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.C[O-].[Na+].[CH2:16]([CH:18]1[O:20][CH2:19]1)Cl>CO>[O:20]1[CH2:19][CH:18]1[CH2:16][O:12][C:1]1[CH:2]=[CH:3][CH:4]=[C:5]2[C:10]=1[CH2:9][CH2:8][CH:7]([OH:11])[CH2:6]2

Komponenten

5

Edukt 3

HCID 7835EpichlorohydrinHCID 10942334Sodium MethoxideHCID 124457385,6,7,8-Tetrahydronaphthalene-1,6-diol

Produkt 1

HCID 124457671,2,3,4-Tetrahydro-5-[2,3-epoxy-propoxy]-2-naphthol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of 2.46 g. (0.015 mole) of 5,6,7,8-tetrahydro-1,6-naphthalenediol and 810 mg. (0.015 mole) of sodium methoxide in 30 ml. of methanol is prepared under nitrogen and the solvent removed in vacuo. The resulting foam is stirred overnight with 20 ml. of dimethylsulfoxide and 1.40 g. (0.015 mole) of epichlorohydrin, poured into 200 ml. of water and extracted with four 125 ml. portions of ether. Drying and solvent removal gives 3.06 g. of oil which is purified by chromatography on silica gel (75 g.). Elution with hexane-chloroform mixtures gives a total of 1.56 g. (49%) of material with one spot on TLC.

Aufarbeitung

  1. customthe solvent removed in vacuo
  2. extractionof water and extracted with four 125 ml
  3. customDrying
  4. customsolvent removal
  5. customgives 3.06 g
  6. customof oil which is purified by chromatography on silica gel (75 g.)
  7. washElution with hexane-chloroform mixtures
  8. customgives a total of 1.56 g

Quellen und Nachweise

ORD-Eintrag
ord-82bbde6c70684b798f9ad8091d3ecd9f
Quelldatensatz
uspto-grants-1979_05
Patentnummer
US04156789

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