Water → 4-(2,3-Dihydroxypropoxy)-3-chlorobenzaldehyde

HRID 38719

Reaktionsgleichung

Reaktionsgleichung von HRID 38719
[CH2:1]([O:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[O:10])=[CH:7][C:6]=1[Cl:13])[CH:2]=[CH2:3].[OH2:14].C[N+]1([O-])CC[O:19]CC1>CC(C)=O.CC(=O)OCC.O=[Os](=O)(=O)=O.C(O)(C)(C)C>[OH:14][CH:2]([CH2:3][OH:19])[CH2:1][O:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[O:10])=[CH:7][C:6]=1[Cl:13]

Komponenten

8

Edukt 3

HCID 962WaterHCID 82029Methyl morpholine oxideHCID 47700363-Chloro-4-(prop-2-en-1-yloxy)benzaldehyde

Produkt 1

HCID 798396484-(2,3-Dihydroxypropoxy)-3-chlorobenzaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 6386tert-ButanolKatalysatorHCID 30318Osmium TetroxideKatalysatorHCID 180AcetoneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

The above 4-allyloxy-3-chloro-benzaldehyde (5.37 g, 27.3 mmol) is dissolved in acetone (100 mL) and water (10 mL) and treated with a 2.5% solution of OsO4 in tert.-butanol (1.71 mL, 0.137 mmol OsO4). N-methyl morpholine-N-oxide (3.87 g, 32.8 mmol) is added and the reaction mixture is stirred at rt for 20 h before it is diluted with EA (300 mL) and washed with 10% aq. citric acid solution (200 mL) and water (2×150 mL). The washings are extracted with EA (300 mL) and the combined organic extracts are dried over MgSO4, filtered and concentrated to furnish the title compound (6.02 g) as beige foam which was used in the following steps without further purification. LC: tR=0.67 min.

Aufarbeitung

  1. washwashed with 10% aq. citric acid solution (200 mL) and water (2×150 mL)
  2. extractionThe washings are extracted with EA (300 mL)
  3. dry with materialthe combined organic extracts are dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-a50a026ccdeb406389225a2375678e72
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524752B2

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