Potassium Carbonate → Methyl 2-(2-chloro-4-hydroxymethyl-6-propylphenoxy)-2-(3,4-methylenedioxyphenyl)acetate

HRID 274932Notes

Reaction equation

HRID 274932 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([CH2:11][CH2:12][CH3:13])[C:9]=1[OH:10])[CH2:5][OH:6].Br[CH:15]([C:20]1[CH:25]=[CH:24][C:23]2[O:26][CH2:27][O:28][C:22]=2[CH:21]=1)[C:16]([O:18][CH3:19])=[O:17].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:5][OH:6])[CH:7]=[C:8]([CH2:11][CH2:12][CH3:13])[C:9]=1[O:10][CH:15]([C:20]1[CH:25]=[CH:24][C:23]2[O:26][CH2:27][O:28][C:22]=2[CH:21]=1)[C:16]([O:18][CH3:19])=[O:17]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11821769Methyl 2-(1,3-benzodioxol-5-yl)-2-bromoacetateHCID 544827242-Chloro-4-(hydroxymethyl)-6-propylphenol

Product 1

HCID 20089199Methyl 2-(2-chloro-4-hydroxymethyl-6-propylphenoxy)-2-(3,4-methylenedioxyphenyl)acetateYield 81%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 0.280 g (1.40 mmol) of the product of step C and 0.762 g () of methyl α-bromo-3,4-methylenedioxyphenylacetate in 3.0 mL of acetone was added 0.386 g (2.80 mmol) of finely powdered potassium carbonate and the mixture was stirred and heated at reflux for 2 hours. At this point, the reaction mixture was cooled to room temperature, filtered, and evaporated in vacuo. The residue was purified on a silica gel flash chromatography column eluted with 30% EtOAc-hexane. Evaporation of the purified fractions and solvent removal in vacuo afforded 0.445 g (81%) of the title compound.

Workup

  1. temperatureheated
  2. temperatureat reflux for 2 hours
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customThe residue was purified on a silica gel flash chromatography column
  6. washeluted with 30% EtOAc-hexane
  7. customEvaporation of the purified fractions and solvent removal in vacuo

Sources & evidence

ORD record
ord-86632db72e4e42329248380881b3b94c
Source dataset
uspto-grants-1995_02
Patent number
US05391566

Reaction notes

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