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

HRID 2113361Notes

Reaction equation

HRID 2113361 reaction equation
[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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 64952,2-DimethoxypropaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-986937248e9d417c9d1cf91b126c5d8b
Source dataset
uspto-grants-2009_04
Patent number
US07524959B2

Reaction notes

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