Reaction #65500

Reaction equation

18-crown-6

p-cresol

methyl 2-bromophenylacetate

→

title compound

Yield 59.3%

Methyl 2-(4-Methylphenoxy)Phenylacetate

Yield 59.3%

Solvents

DMF

DMF

DMF

Conditions

Workup

1. 1
   Otherthe reaction 45 minutes until the foaming subsides
2. 2
   Otherresulting in a purple solution that
3. 3
   workup.STIRRINGThe reaction mixture was stirred 2.5 hours
4. 4
   Concentrationwas then concentrated in vacuo
5. 5
   OtherThe residue was chromatographed on a flash silica column (130×30 mm)
6. 6
   Washeluted with 5% ethyl actate/hexane

Procedure

To a suspension of KH (212 mg, 1.0 eq) in DMF (3 mL) was added a solution of p-cresol (200 mg; 1.85 mmol) in DMF (2 mL) followed by 18-crown-6 (50 mg, 0.2 eq). After stirring the reaction 45 minutes until the foaming subsides, a solution of methyl 2-bromophenylacetate (424 mg, 1.0 eq) in DMF (1 mL) was added, resulting in a purple solution that slowly faded to yellow. The reaction mixture was stirred 2.5 hours and was then concentrated in vacuo. The residue was chromatographed on a flash silica column (130×30 mm) eluted with 5% ethyl actate/hexane to yield 281 mg (62%) of the title compound (Rf =0.38, 5% ethyl acetate/hexane).

Source