Ethyl Acetate → Methyl 2-(2-chloro-4-methylphenoxy)-2-phenylacetate

HRID 2399472Notes

Reaction equation

HRID 2399472 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[C:8]([CH3:10])[CH:7]=[CH:6][C:5]=1[OH:11].Br[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH2:19][C:20]([O:22][CH3:23])=[O:21].C(OCC)(=O)C>CN(C=O)C>[Cl:3][C:4]1[CH:9]=[C:8]([CH3:10])[CH:7]=[CH:6][C:5]=1[O:11][CH:19]([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:13]=1)[C:20]([O:22][CH3:23])=[O:21]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 148512-Chloro-4-methylphenolHCID 24758Sodium hydrideHCID 8063364Methyl 2-(2-bromophenyl)acetate

Product 1

HCID 19385673Methyl 2-(2-chloro-4-methylphenoxy)-2-phenylacetateYield 83.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of 0.282 g (7.04 mmol) of a 60% oil dispersion of sodium hydride in DMF was added 1.00 g (7.04 mmol) of 2-chloro-4-methylphenol and the mixture was stirred under an N2 atmosphere at room temperature. After 10 minutes, a solution of 1.94 g (8.45 mmol) of methyl 2-bromophenylacetate dissolved in 10 mL of DMF was added and the reaction was stirred an additional 1.5 hours. The reaction was then diluted into ethyl acetate, washed with water, dried (MgSO4), filtered and evaporated. The residue was purified on a silica gel flash chromatography column eluted with 4% ethyl acetate/hexane to afford 1.70 g (83%) of the title compound.

Workup

  1. additionwas added
  2. stirringthe reaction was stirred an additional 1.5 hours
  3. washwashed with water
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified on a silica gel flash chromatography column
  8. washeluted with 4% ethyl acetate/hexane

Sources & evidence

ORD record
ord-ffc5a5a6d7af49a1b63f3d20b087954d
Source dataset
uspto-grants-1995_09
Patent number
US05449682

Reaction notes

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