Ammonia → 2-Cyclohexyl-2-hydroxymethylpropan-1,3-diol

HRID 129272Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 129272
C([O:8][CH2:9][C:10]([CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1)([CH2:13][OH:14])[CH2:11][OH:12])C1C=CC=CC=1.N.[Na].[Cl-].[NH4+]>C(OCC)C>[CH:15]1([C:10]([CH2:9][OH:8])([CH2:11][OH:12])[CH2:13][OH:14])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1

Komponenten

6

Edukt 4

HCID 222AmmoniaHCID 25517Ammonium ChlorideHCID 5360545SodiumHCID 193733732-Benzyloxymethyl-2-cyclohexylpropan-1,3-diol

Produkt 1

HCID 129305402-Cyclohexyl-2-hydroxymethylpropan-1,3-diol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

2-Benzyloxymethyl-2-cyclohexyl-propan-1,3-diol (5.5 g.) in dry diethyl ether (50 ml.) was added to liquid ammonia (200 ml) at -70°. Sodium (2.5 g.) was added to the stirred solution. Stirring was maintained at -70° for 1 hour. The mixture was allowed to warm up to 0° and solid ammonium chloride (15 g.) was added cautiously. The ammonia was removed from the reaction mixture under a current of nitrogen. Methanol (25 ml.) was added to the stirred mixture to destroy residual sodium. Dichloromethane (400 ml) was added and the mixture was filtered. The filtrates were evaporated in vacuo. 2-Cyclohexyl-2-hydroxymethylpropan-1,3-diol was obtained as a colourless solid (3.2 g.).

Aufarbeitung

  1. temperaturewas maintained at -70° for 1 hour
  2. temperatureto warm up to 0°
  3. customThe ammonia was removed from the reaction mixture under a current of nitrogen
  4. additionMethanol (25 ml.) was added to the stirred mixture
  5. customto destroy residual sodium
  6. additionDichloromethane (400 ml) was added
  7. filtrationthe mixture was filtered
  8. customThe filtrates were evaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-f06e67b395724764a8f9c0e91a1fb3d2
Quelldatensatz
uspto-grants-1995_11
Patentnummer
US05466710

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