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

Reaction equation

[CH:1]1[C:6]([OH:7])=[CH:5][CH:4]=[C:3]([CH3:8])[CH:2]=1.C1OCCOCCOCCOCCOCCOC1.Br[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[CH2:34][C:35]([O:37][CH3:38])=[O:36]>CN(C=O)C>[CH3:8][C:3]1[CH:4]=[CH:5][C:6]([O:7][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[CH2:34][C:35]([O:37][CH3:38])=[O:36])=[CH:1][CH:2]=1

Participants

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).