Benzene → Methyl 4-(tetrahydropyran-2-yloxy)phenylacetate

Participants

Reaction Steps

A mixture of 38.5 g. of methyl 4-hydroxyphenylacetate, 3.8 l. of benzene and 0.9 g. of p-toluenesulfonic acid is heated to the boiling point and about 20 ml. of solvent are distilled to remove moisture, it is then cooled to room temperature and treated with 130 ml. of freshly distilled dihydropyran. The reaction mixture is kept at room temperature for 1 hour and washed with 10% sodium bicarbonate solution and water, dried over sodium sulfate and evaporated to dryness under reduced pressure. The residue is dissolved in methylene chloride and filtered through neutral alumina, thus obtaining the pure methyl 4-(tetrahydropyran-2-yloxy)phenylacetate.

Provenance & Evidence