Réaction #65500

Équation de réaction

18-crown-6

p-cresol

methyl 2-bromophenylacetate

→

title compound

Rendement 59.3%

Methyl 2-(4-Methylphenoxy)Phenylacetate

Rendement 59.3%

Solvants

DMF

DMF

DMF

Conditions de réaction

Traitement

1. 1
   Autrethe reaction 45 minutes until the foaming subsides
2. 2
   Autreresulting 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
   AutreThe residue was chromatographed on a flash silica column (130×30 mm)
6. 6
   Lavageeluted with 5% ethyl actate/hexane

Mode opératoire

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