P-Cresol → Methyl 2-(4-methylphenoxy)phenylacetate

HRID 2255563Notes

Reaction equation

HRID 2255563 reaction equation
[CH:1]1[C:6]([OH:7])=[CH:5][CH:4]=[C:3]([CH3:8])[CH:2]=1.Br[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH2:16][C:17]([O:19][CH3:20])=[O:18]>CN(C=O)C.C1OCCOCCOCCOCCOCCOC1>[CH3:8][C:3]1[CH:4]=[CH:5][C:6]([O:7][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[CH2:16][C:17]([O:19][CH3:20])=[O:18])=[CH:1][CH:2]=1

Participants

5

Reactant 2

HCID 2879P-CresolHCID 8063364Methyl 2-(2-bromophenyl)acetate

Product 1

HCID 13729875Methyl 2-(4-methylphenoxy)phenylacetateYield 58%

Reagents, catalysts & solvents 2

HCID 2855718-Crown-6CatalystHCID 6228DimethylformamideSolvent3×

Procedure

To a cooled (0° C.) suspension of KH (2.12 g, 1.0 eq) in DMF (30 mL) was added a solution of p-cresol (2.00 g, 18.5 mmol) in 20 mL of DMF. The reaction mixture was stirred 15 minutes, then 18-crown-6 (200 mg) was added followed by a solution of 4.24 g (18.5 mmol) of methyl 2-bromophenylacetate dissolved in 10 mL of DMF. The reaction mixture was stirred 45 minutes, then partitioned between ethyl acetate and water. The organic layer was washed with water, brine, dried (MgSO4), filtered and evaporated in vacuo. The residue was purified on a silica gel flash chromatography column (150×40 mm) eluted with 5% ethyl acetate/hexane to yield 2.63 g (58%) of the title compound.

Workup

  1. temperatureTo a cooled
  2. stirringThe reaction mixture was stirred 45 minutes
  3. custompartitioned between ethyl acetate and water
  4. washThe organic layer was washed with water, brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customThe residue was purified on a silica gel flash chromatography column (150×40 mm)
  9. washeluted with 5% ethyl acetate/hexane

Sources & evidence

ORD record
ord-90c23319c1244a38bda278ca9c573974
Source dataset
uspto-grants-1993_08
Patent number
US05240938

Reaction notes

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