Acetone → 1,3-dibutoxybenzene

HRID 490151Notes

Reaction equation

HRID 490151 reaction equation
[CH2:1](Br)[CH2:2][CH2:3][CH3:4].[C:6](=[O:9])([O-])[O-].[K+].[K+].[C:12]1([CH:19]=[CH:18][CH:17]=[C:15]([OH:16])[CH:14]=1)O.[Cl-].[NH4+].[CH3:22][C:23]([CH3:25])=O>>[CH2:1]([O:16][C:15]1[CH:17]=[CH:18][CH:19]=[C:12]([O:9][CH2:6][CH2:22][CH2:23][CH3:25])[CH:14]=1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 5

HCID 180AcetoneHCID 5054ResorcinolHCID 8002Butyl bromideHCID 11430Potassium CarbonateHCID 25517Ammonium Chloride

Product 1

HCID 110961901,3-dibutoxybenzene

Conditions

Temperature
90 °C

Procedure

25.5 g of butyl bromide was added to a 150 mL acetone solution of 26.4 g of potassium carbonate and 10.0 g of resorcinol, after which the reaction mixture was stirred for 6 hours at 90° C. 100 mL of a saturated ammonium chloride aqueous solution was poured into the reaction solution under stirring, following by 30 minutes more stirring, after which the solvent was distilled off under reduced pressure. 200 mL of water was added, after which extraction was performed with ethyl acetate (200 mL×3). The organic layer was washed with saturated brine and dried with magnesium sulfate, and the drying agent was then filtered off and the solvent was distilled off under reduced pressure. The residue thus obtained was separated and purified by column chromatography (silica gel 60, mobile phase: hexane/ethyl acetate=95/5 to 1/1; v/v) to obtain 11.0 g of the titled compound (colorless oily substance).

Workup

  1. stirringunder stirring
  2. waitfollowing by 30 minutes
  3. stirringmore stirring
  4. distillationafter which the solvent was distilled off under reduced pressure
  5. addition200 mL of water was added
  6. extractionafter which extraction
  7. washThe organic layer was washed with saturated brine
  8. dry with materialdried with magnesium sulfate
  9. filtrationthe drying agent was then filtered off
  10. distillationthe solvent was distilled off under reduced pressure
  11. customThe residue thus obtained
  12. customwas separated
  13. custompurified by column chromatography (silica gel 60, mobile phase: hexane/ethyl acetate=95/5 to 1/1; v/v)

Sources & evidence

ORD record
ord-22af83c0f6c646b08dc6feaa26da6611
Source dataset
uspto-grants-2009_05
Patent number
US07528124B2

Reaction notes

Loading…