Acetone → Methyl 3-bromo-5-(1,2-dihydroxyethyl)benzoate

HRID 1845309Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1845309
[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=C(C=C)[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].C[N+]1([O-])CC[O:18]CC1.[O-]S([O-])(=S)=O.[Na+].[Na+].[CH3:29][C:30]([CH3:32])=[O:31]>O.[Os](=O)(=O)(=O)=O>[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:29]([CH:30]([OH:31])[CH2:32][OH:18])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6]

Komponenten

7

Edukt 4

HCID 180AcetoneHCID 24477Sodium ThiosulfateHCID 82029Methyl morpholine oxideHCID 58188041Methyl 3-bromo-5-vinylbenzoate

Produkt 1

HCID 58188335Methyl 3-bromo-5-(1,2-dihydroxyethyl)benzoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 30318Osmium TetroxideKatalysatorHCID 962WaterLösungsmittel2×

Versuchsvorschrift

To a stirred solution of methyl 3-bromo-5-vinylbenzoate (1.6 g, 6.6 mmol) and N-methylmorpholine N-oxide (2.0 g, 17.1 mmol) in acetone (40 mL) and water (10 mL) was added dropwise a 5% solution of osmium tetraoxide in water (0.50 g, 0.10 mmol). The reaction mixture was stirred at rt for 3 h, and then a saturated aq. Na2S2O3 solution was added. After being stirred for 30 min, the reaction mixture was extracted with EtOAc (100 mL×3). The combined organic layers were washed with water and brine, dried, and concentrated. The residue was purified by flash column to afford the title compound.

Aufarbeitung

  1. stirringAfter being stirred for 30 min
  2. extractionthe reaction mixture was extracted with EtOAc (100 mL×3)
  3. washThe combined organic layers were washed with water and brine
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified by flash column

Quellen und Nachweise

ORD-Eintrag
ord-fae21d0f18f648d9a4efd15ec940dc02
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08946439B2

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