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1-Pentanol → 2-(2,3-Dimethoxyphenoxy)acetophenone

HRID 3682
Notes
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Reaction equation

HRID 3682 reaction equation
C(O)CCCC.[CH3:7][O:8][C:9]1[C:14]([O:15][CH3:16])=[CH:13][CH:12]=[CH:11][C:10]=1[OH:17].Br[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[C:25](=[O:27])[CH3:26].C(=O)([O-])[O-].[K+].[K+]>C([O-])(=O)C.[Cu+2].C([O-])(=O)C.C(OCC)(=O)C>[CH3:7][O:8][C:9]1[C:14]([O:15][CH3:16])=[CH:13][CH:12]=[CH:11][C:10]=1[O:17][CH2:26][C:25]([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:19]=1)=[O:27]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 62761-PentanolHCID 11430Potassium CarbonateHCID 750602'-BromoacetophenoneHCID 788282,3-Dimethoxyphenol

Product 1

HCID 183799552-(2,3-Dimethoxyphenoxy)acetophenoneYield 87%

Reagents, catalysts & solvents 2

HCID 8895
Cupric acetate
Catalyst
HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
150 °C

Procedure

Amyl alcohol (44 ml) was added to 2,3-dimethoxyphenol (5 g), 2'-bromoacetophenone (7 g), potassium carbonate (6.7 g) and copper acetate (1.1 g), followed by heating and stirring at 150° C. for 8 hours for reacting them together. To the reaction solution was added ethyl acetate (300 ml), and the resulting solution was washed in dilute hydrochloric acid, in water, and in a saturated sodium chloride solution, and dried over anhydrous magnesium sulfate, and the solvents therein were distilled off under reduced pressure. The residue was purified by silica gel column chromatography (developing solvent: hexane:ethyl acetate=8:1), to recover 2-(2,3-dimethoxyphenoxy)acetophenone (7.6 g; yield of 87%). By 1H-NMR (90 MHz, CDCl3), the compound has the peaks shown below.

Workup

  1. temperatureby heating
  2. washthe resulting solution was washed in dilute hydrochloric acid, in water
  3. dry with materialin a saturated sodium chloride solution, and dried over anhydrous magnesium sulfate
  4. distillationthe solvents therein were distilled off under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (developing solvent: hexane:ethyl acetate=8:1)

Sources & evidence

ORD record
ord-b4abd6c40e154847ac62183456b57efd
Source dataset
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05734067

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes