P-Cresol → Methyl 2-(2-chlorophenyl)-2-(4-methylphenoxy)acetate

HRID 257842Notes

Reaction equation

HRID 257842 reaction equation
[H-].[K+].[CH:3]1[C:8]([OH:9])=[CH:7][CH:6]=[C:5]([CH3:10])[CH:4]=1.Br[CH:12]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[Cl:23])[C:13]([O:15][CH3:16])=[O:14]>CN(C=O)C.C1OCCOCCOCCOCCOCCOC1>[Cl:23][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[CH:12]([O:9][C:8]1[CH:7]=[CH:6][C:5]([CH3:10])=[CH:4][CH:3]=1)[C:13]([O:15][CH3:16])=[O:14]

Participants

6

Reactant 3

HCID 2879P-CresolHCID 82127Potassium hydrideHCID 10730282Methyl alpha-bromo-2-chlorophenylacetate

Product 1

HCID 19385716Methyl 2-(2-chlorophenyl)-2-(4-methylphenoxy)acetateYield 77%

Reagents, catalysts & solvents 2

HCID 2855718-Crown-6CatalystHCID 6228DimethylformamideSolvent2×

Procedure

To a stirred (0° C.) suspension of 0.530 g (4.63 mmol) of a 35% oil dispersion of potassium hydride in 5 mL of anhydrous DMF was added 0.50 g (4.63 mmol) of p-cresol and 0.050 g of 18-crown-6. After stirring at room temperature for 15 minutes, a solution of 1.22 g (4.63 mmol) of the product of Step B in 5 mL of DMF was slowly added. The reaction mixture was stirred and allowed to warm to room temperature during 45 minutes. The reaction mixture was then partitioned between ethyl acetate and water, separated, dried (MgSO4), filtered and evaporated in vacuo. The residue was purified on a silica gel flash chromatography column eluted with 5% ethyl acetate/hexane to afford 1.03 g (77%) of the title compound.

Workup

  1. stirringAfter stirring at room temperature for 15 minutes
  2. stirringThe reaction mixture was stirred
  3. customThe reaction mixture was then partitioned between ethyl acetate and water
  4. customseparated
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customThe residue was purified on a silica gel flash chromatography column
  9. washeluted with 5% ethyl acetate/hexane

Sources & evidence

ORD record
ord-2fb24d59f9dc486b939a042014e9b767
Source dataset
uspto-grants-1993_11
Patent number
US05264439

Reaction notes

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