Acetone → 4-[(4-Bromophenoxy)methyl]-2,2,4-trimethyl-1,3-dioxolane

HRID 1909092

Reaction equation

HRID 1909092 reaction equation
[Br:1][C:2]1[CH:14]=[CH:13][C:5]([O:6][CH2:7][C:8]([CH3:12])([OH:11])[CH2:9][OH:10])=[CH:4][CH:3]=1.[CH3:15][C:16]([CH3:18])=O>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH2:7][C:8]2([CH3:12])[CH2:9][O:10][C:16]([CH3:18])([CH3:15])[O:11]2)=[CH:13][CH:14]=1

Participants

3

Reactant 2

HCID 180AcetoneHCID 71059322HCID 71059322, compound

Product 1

HCID 710593314-[(4-Bromophenoxy)methyl]-2,2,4-trimethyl-1,3-dioxolaneYield 61%

Procedure

3-(4-Bromophenoxy)-2-methylpropane-1,2-diol (261 mg, 1.00 mmol), acetone (10 mL), and a boron trifluoride diethyl ether complex (3 drops) were mixed. The mixture was then stirred at room temperature for 14 hours. A residue was obtained by concentrating the mixture under reduced pressure, and ethyl acetate and water were added thereto, followed by extraction. The organic layer was washed with a saline solution twice. A residue was obtained by concentrating the organic layer under reduced pressure, and the resulting residue was then subjected to chromatography refining (methylene chloride) using silica gel, obtaining 183 mg of the objective compound (yield: 61%).

Workup

  1. customA residue was obtained
  2. concentrationby concentrating the mixture under reduced pressure, and ethyl acetate and water
  3. additionwere added
  4. extractionfollowed by extraction
  5. washThe organic layer was washed with a saline solution twice
  6. customA residue was obtained
  7. concentrationby concentrating the organic layer under reduced pressure

Sources & evidence

ORD record
ord-0f7ff5355e9c4c48ba7e825ef06f81e9
Source dataset
uspto-grants-2013_12
Patent number
US08598358B2

Linked notes

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