Acetone → 6-Bromo-2,2-dimethyl-4H-benzo[d][1,3]dioxine

HRID 490991

Reaktionsgleichung

Reaktionsgleichung von HRID 490991
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:10])=[C:6]([CH:9]=1)[CH2:7][OH:8].[CH3:11][C:12]([CH3:14])=O.[OH-].[Na+].C(OCC)C>COC(OC)(C)C.[Cl-].[Zn+2].[Cl-]>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][C:12]([CH3:14])([CH3:11])[O:8][CH2:7][C:6]=2[CH:9]=1

Komponenten

7

Edukt 4

HCID 180AcetoneHCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 753425-Bromo-2-hydroxybenzyl alcohol

Produkt 1

HCID 145203386-Bromo-2,2-dimethyl-4H-benzo[d][1,3]dioxine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3007855ZincchlorideKatalysatorHCID 64952,2-DimethoxypropaneLösungsmittel

Versuchsvorschrift

To 5-bromo-2-hydroxybenzyl alcohol (93 g, 0.46 mol, available from Sigma-Aldrich) in 2.0 L of 2,2-dimethoxypropane was added 700 mL of acetone, followed by zinc chloride (170 g). After stirring for 18 hours, 1.0 M aqueous sodium hydroxide was added until the aqueous phase was basic. Diethyl ether (1.5 L) was added to the slurry and the organic phase was decanted into a separatory funnel. The organic phase was washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure to give the title compound as an oil.

Aufarbeitung

  1. customthe organic phase was decanted into a separatory funnel
  2. washThe organic phase was washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-24c3fb42e0934fb991e8732fbc4a985d
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07528253B2

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