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

HRID 1936216Notes

Reaction equation

HRID 1936216 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:7]([OH:10])=[CH:8][CH:9]=1)[CH2:5][OH:6].[Al+3].[Cl-].[Cl-].[Cl-].[OH-].[Na+].[CH3:17][C:18]([CH3:20])=O>CCOCC>[CH3:17][C:18]1([CH3:20])[O:6][CH2:5][C:4]2[CH:3]=[C:2]([Br:1])[CH:9]=[CH:8][C:7]=2[O:10]1

Participants

6

Reactant 4

HCID 180AcetoneHCID 14798Sodium HydroxideHCID 753425-Bromo-2-hydroxybenzyl alcoholHCID 6451240Aluminum(III) Chloride

Product 1

HCID 145203386-Bromo-2,2-dimethyl-4H-benzo[d][1,3]dioxineYield 81%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 5.0 g (24.63 mmol) 3-bromo-6-hydroxybenzyl alcohol in 30 ml acetone cooled to 0° C., a solution of 1.15 g (8.62 mmol) AlCl3 in 20 ml Et2O is added dropwise. The resulting mixture is allowed to stand at room temperature for 1 hr, after which time it is cooled to 0° C. and 50 ml of a 10% NaOH aqueous solution previously cooled to 5° C. is added thereto. The separated Et2O phase is washed twice with 20 ml H2O, dried on anhydrous Na2SO4, evaporated to dryness and distilled under reduce pressure to yield 4.85 g (81%) 2,2-dimethyl-6-bromobenzo-1,3-dioxane as an oil.

Workup

  1. additionis added
  2. washThe separated Et2O phase is washed twice with 20 ml H2O
  3. dry with materialdried on anhydrous Na2SO4
  4. customevaporated to dryness
  5. distillationdistilled

Sources & evidence

ORD record
ord-7241a0750c8a4399931a9bd2b3f4037c
Source dataset
uspto-grants-2002_05
Patent number
US06388134B1

Reaction notes

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