Toluene → HCID 10064622, Verbindung

HRID 1029544Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1029544
[C:1](Cl)(Cl)=[O:2].C1(C)C=CC=CC=1.[CH3:12][C:13]([C:16]1[CH:17]=[C:18]([CH:25]=[C:26]([C:29]([CH3:32])([CH3:31])[CH3:30])[C:27]=1[OH:28])[O:19][CH2:20][C:21]([NH:23][NH2:24])=[O:22])([CH3:15])[CH3:14]>O1CCCC1.C(OCC)(=O)C>[CH3:15][C:13]([C:16]1[CH:17]=[C:18]([CH:25]=[C:26]([C:29]([CH3:32])([CH3:31])[CH3:30])[C:27]=1[OH:28])[O:19][CH2:20][C:21]1[O:22][C:1](=[O:2])[NH:24][N:23]=1)([CH3:12])[CH3:14]

Komponenten

6

Edukt 3

HCID 1140TolueneHCID 6371PhosgeneHCID 10424537HCID 10424537, Verbindung

Produkt 1

HCID 10064622HCID 10064622, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A 12.5% solution of phosgene in toluene (2.4 mL, 2.7 mmol) is added dropwise to a -78° C. of [3,5-bis(1,1-dimethylethyl)-4-hydroxyphenoxy]-acetic acid hydrazide (0.40 g, 1.36 mmol) in tetrahydrofuran (25 mL). The reaction mixture is stirred for 30 minutes, diluted with ethyl acetate, and washed three times with water and once with brine. Drying the organic phase over magnesium sulfate and evaporation gives a pale yellow oil which is crystallized from ethyl acetate/hexane yielding 0.34 g (79%) of 5-[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenoxy]methyl-1,3,4-oxadiazol-2(3H)-one; mp 138.0°-140.0° C.

Aufarbeitung

  1. washwashed three times with water
  2. customDrying the organic phase
  3. customover magnesium sulfate and evaporation
  4. customgives a pale yellow oil which
  5. customis crystallized from ethyl acetate/hexane yielding 0.34 g (79%) of 5-[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenoxy]methyl-1,3,4-oxadiazol-2(3H)-one

Quellen und Nachweise

ORD-Eintrag
ord-69a8454c079b4dd4bf484a5f631b85ba
Quelldatensatz
uspto-grants-1992_04
Patentnummer
US05102897

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