Benzyl chloroformate → Carbamic acid, (6-hydroxyhexyl)-, phenylmethyl ester

HRID 376105

Reaktionsgleichung

Reaktionsgleichung von HRID 376105
[CH2:1]([O:8][C:9](Cl)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][OH:19].C(=O)([O-])O.[Na+]>CC(C)=O.O>[CH2:1]([O:8][C:9]([NH:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][OH:19])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

6

Edukt 3

HCID 10387Benzyl chloroformateHCID 199606-Amino-1-hexanolHCID 516892Sodium Bicarbonate

Produkt 1

HCID 4184071Carbamic acid, (6-hydroxyhexyl)-, phenylmethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

7.06 ml (47 mmol) of chloroformic acid benzyl ester are added dropwise to a solution of 5.52 g (47 mmol) of 6-aminohexan-1-ol and 3.95 g (47 mmol) of sodium hydrogen carbonate in 100 ml of acetone and 50 ml of water. The mixture is stirred at room temperature for 18 hours and concentrated to approximately 70 ml, and the white precipitate is filtered off, washed with approximately 20 ml of water, taken up in 250 ml of methylene chloride and dried over magnesium sulfate; the magnesium sulfate is filtered off and the residue is concentrated to dryness by evaporation. 6-(N-benzyloxycarbonylamino)hexan-1-ol is obtained in the form of white crystals having a melting point of 58°-60°.

Aufarbeitung

  1. concentrationconcentrated to approximately 70 ml
  2. filtrationthe white precipitate is filtered off
  3. washwashed with approximately 20 ml of water
  4. dry with materialdried over magnesium sulfate
  5. filtrationthe magnesium sulfate is filtered off
  6. concentrationthe residue is concentrated to dryness by evaporation

Quellen und Nachweise

ORD-Eintrag
ord-936b247750754cecb261202c8f1c2d6c
Quelldatensatz
uspto-grants-1996_01
Patentnummer
US05488140

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