Potassium Carbonate → Methyl alpha-(2-n-propyl-4-cyanophenoxy)-3,4-methylenedioxyphenylacetate

HRID 865548Notes

Reaction equation

HRID 865548 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[CH2:10][CH2:11][CH3:12].C(=O)([O-])[O-].[K+].[K+].Br[CH:20]([C:25]1[CH:30]=[CH:29][C:28]2[O:31][CH2:32][O:33][C:27]=2[CH:26]=1)[C:21]([O:23][CH3:24])=[O:22]>CC(C)=O>[CH2:10]([C:3]1[CH:4]=[C:5]([C:6]#[N:7])[CH:8]=[CH:9][C:2]=1[O:1][CH:20]([C:25]1[CH:30]=[CH:29][C:28]2[O:31][CH2:32][O:33][C:27]=2[CH:26]=1)[C:21]([O:23][CH3:24])=[O:22])[CH2:11][CH3:12]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11821769Methyl 2-(1,3-benzodioxol-5-yl)-2-bromoacetateHCID 139876694-hydroxy-3-propylBenzonitrile

Product 1

HCID 22912470Methyl alpha-(2-n-propyl-4-cyanophenoxy)-3,4-methylenedioxyphenylacetate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred solution of 4.50 g (27.95 mmol) of the product of Step B in 30 mL of acetone was added 4.64 g (33.54 mmol) of powdered potassium carbonate and the reaction mixture was stirred for 10 minutes. Methyl α-bromo-3,4-methylenedioxyphenylacetate (8.01 g; 29.35 mmol) was then added and the reaction mixture refluxed overnight. The reaction mixture was cooled, filtered, and the filtrate evaporated in vacuo, dried in a vacuum to afford 10.30 g (9.87 g theoretical) of the title compound which was used without purification in the next step.

Workup

  1. temperaturethe reaction mixture refluxed overnight
  2. temperatureThe reaction mixture was cooled
  3. filtrationfiltered
  4. customthe filtrate evaporated in vacuo
  5. customdried in a vacuum

Sources & evidence

ORD record
ord-8210ae82f6364f148ae2be9d6ca879ce
Source dataset
uspto-grants-1996_10
Patent number
US05565485

Reaction notes

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