P-Cresol → 3-[4-(2-Hydroxyethoxy)phenyl]-5-methylbenzofuran-2-one
Reaction equation
[OH:1][CH2:2][CH2:3][O:4][C:5]1[CH:15]=[CH:14][C:8]([CH:9](O)[C:10]([OH:12])=[O:11])=[CH:7][CH:6]=1.[CH:16]1[C:21](O)=[CH:20][CH:19]=[C:18]([CH3:23])[CH:17]=1>O>[OH:1][CH2:2][CH2:3][O:4][C:5]1[CH:15]=[CH:14][C:8]([CH:9]2[C:16]3[CH:17]=[C:18]([CH3:23])[CH:19]=[CH:20][C:21]=3[O:12][C:10]2=[O:11])=[CH:7][CH:6]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A suspension of 8.5 g (40.0 mmol) of 4-(2-hydroxyethoxy)mandelic acid (compound (201), Example 10, Table 2) and 12.0 g (110 mmol) of p-cresol is maintained at 180° C. under a nitrogen atmosphere for 75 minutes, during which the water formed distils off. Excess p-cresol is then distilled off in a vacuum rotary evaporator. Chromatography of the residue on silica gel using the eluent system 9:1 dichloromethane/ethyl acetate gives 6.6 g (58%) of 3-[4-(2-hydroxyethoxy)phenyl]-5-methylbenzofuran-2-one, a yellowish resin (compound (119), Table 1).