Acetone → 4-(2,3-Dihydroxypropoxy)benzaldehyde

HRID 1466198

Reaktionsgleichung

Reaktionsgleichung von HRID 1466198
C([O:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[O:10])=[CH:7][CH:6]=1)C=C.C[N+]1([O-])CC[O:17]CC1.[CH3:21][C:22]([CH3:24])=[O:23]>O.C(O)(C)(C)C.CC(=O)OCC.O=[Os](=O)(=O)=O>[OH:23][CH:22]([CH2:24][OH:17])[CH2:21][O:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[O:10])=[CH:7][CH:6]=1

Komponenten

8

Edukt 3

HCID 180AcetoneHCID 82029Methyl morpholine oxideHCID 959424-(Allyloxy)benzaldehyde

Produkt 1

HCID 166558484-(2,3-Dihydroxypropoxy)benzaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 30318Osmium TetroxideKatalysatorHCID 962WaterLösungsmittelHCID 6386tert-ButanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 4-allyloxybenzaldehyde (1.0 g, 6.17 mmol) in acetone (40 mL) and water (5 mL) is added a 2.5% solution of OsO4 in tert. butanol (1.25 mL) followed by N-methyl morpholine-N-oxide (867 mg, 7.4 mmol). The pale yellow solution is stirred at rt for 6 h, diluted with EA (250 mL) and washed with 10% aq. citric acid solution (100 mL) and water (2×100 mL). The washings are extracted with EA (150 mL). The combined organic extracts are concentrated and purified by column chromatography on silica gel to give the title compound (731 mg) as a turbid oil. The title compound reversibly polymerizes upon standing. LC-MS: tR=0.58 min, [M+1+CH3CN]+=238.

Aufarbeitung

  1. washwashed with 10% aq. citric acid solution (100 mL) and water (2×100 mL)
  2. extractionThe washings are extracted with EA (150 mL)
  3. concentrationThe combined organic extracts are concentrated
  4. custompurified by column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-322d82a83a5e44dbb40f864e04198670
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09000018B2

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