Diethyl Ether → 1a,2,7,7a-Tetrahydronaphtho[2,3-b]oxiren-3-ol

HRID 437044

Reaktionsgleichung

Reaktionsgleichung von HRID 437044
ClC1C=CC=C(C(OO)=[O:9])C=1.[C:12]1([OH:22])[C:21]2[CH2:20][CH:19]=[CH:18][CH2:17][C:16]=2[CH:15]=[CH:14][CH:13]=1.CCOCC.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[O:9]1[CH:19]2[CH:18]1[CH2:17][C:16]1[CH:15]=[CH:14][CH:13]=[C:12]([OH:22])[C:21]=1[CH2:20]2

Komponenten

6

Edukt 4

HCID 3283Diethyl EtherHCID 70297m-Chloroperbenzoic acidHCID 974665,8-Dihydro-1-naphtholHCID 516892Sodium Bicarbonate

Produkt 1

HCID 124457371a,2,7,7a-Tetrahydronaphtho[2,3-b]oxiren-3-olAusbeute 40,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

An amount of 25.0 g of m-chloroperbenzoic acid is added over 10 minutes to an ice-cooled solution of 14.6 g of 5,8-dihydro-1-naphthol (prepared as described in Org. Syn., Coll. Vol. IV. pg. 887) in 225 ml of ethyl acetate. After 16 hours at ambient temperature the slurry is poured into a cooled, stirred mixture of 300 ml each of ether and 10% sodium bicarbonate. After 15 minutes the organic phase is separated, washed with water, saturated salt solution and dried. Solvent removal gives an oil which is triturated with two 100 ml portions of boiling hexane. The residue is recrystallized from 150 ml of 1:1 hexane-ethyl acetate to give 6.6 g of 5,6,7,8-tetrahydro-6,7-epoxy-1-naphthol, melting point 143°-146° C. Two further recrystallizations of a small sample give the analytical sample melting point 149.5°-151° C.

Aufarbeitung

  1. additionAfter 16 hours at ambient temperature the slurry is poured into a cooled
  2. customAfter 15 minutes the organic phase is separated
  3. washwashed with water, saturated salt solution
  4. customdried
  5. customSolvent removal
  6. customgives an oil which
  7. customis triturated with two 100 ml portions of boiling hexane
  8. customThe residue is recrystallized from 150 ml of 1:1 hexane-ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-c034390053d940d4a6987a75d58dc3b2
Quelldatensatz
uspto-grants-1977_06
Patentnummer
US04029676

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