Potassium Carbonate → Methyl 2-(2,6-dimethyl-4-formylphenoxy)-2-(3-chlorophenyl)acetate

HRID 1492644Notes

Reaction equation

HRID 1492644 reaction equation
Br[CH:2]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([Cl:13])[CH:8]=1)[C:3]([O:5][CH3:6])=[O:4].[CH3:14][C:15]1[CH:16]=[C:17]([CH:20]=[C:21]([CH3:24])[C:22]=1[OH:23])[CH:18]=[O:19].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:24][C:21]1[CH:20]=[C:17]([CH:18]=[O:19])[CH:16]=[C:15]([CH3:14])[C:22]=1[O:23][CH:2]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([Cl:13])[CH:8]=1)[C:3]([O:5][CH3:6])=[O:4]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 752223,5-Dimethyl-4-hydroxybenzaldehydeHCID 19385736Methyl 2-bromo-2-(3-chlorophenyl)acetate

Product 1

HCID 18950590Methyl 2-(2,6-dimethyl-4-formylphenoxy)-2-(3-chlorophenyl)acetateYield 95%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 1.260 g (4.80 mmol) of methyl α-bromo-(3-chlorophenyl)acetate and 0.600 g (4.00 mmol) of 3,5-dimethyl-4-hydroxybenzaldehyde in 16 mL acetone was added 1.10 g (8.00 mmol) of potassium carbonate and the resulting mixture was stirred and heated at reflux for 3.5 hours. The reaction mixture was cooled to room temperature, filtered and concentrated in vacuo. The residue was purified on a silica gel flash chromatography column eluted with 30% EtOAc-hexane. The purified fractions were combined, evaporated and dried in vacuo to afford 1.260 g (95%) of the title compound.

Workup

  1. temperatureheated
  2. temperatureat reflux for 3.5 hours
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified on a silica gel flash chromatography column
  6. washeluted with 30% EtOAc-hexane
  7. customevaporated
  8. customdried in vacuo

Sources & evidence

ORD record
ord-42a21564d6a14c1e8a8fc3797b0f7888
Source dataset
uspto-grants-1994_12
Patent number
US05374638

Reaction notes

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