Toluene → 4-Methoxyphenylacetic Acid

Participants

Reaction Conditions

Reaction Steps

1.44 equivalents (7.7 g) of sodium periodate NaIO4, 0.6 mol % (0.045 g) of sodium dichromate Na2Cr2O72H2O and 3 g of 1N sulfuric acid H2SO4 (12 mol %) were dissolved in 50 ml of water. To this solution were added 25 mmol (3.75 g) of 4-methoxyphenylacetaldehyde and 25 ml of toluene, whereupon the reaction mixture was stirred for 17 h at 20° C. The phases were then separated and the aqueous phase was extracted with 2×10 ml of toluene. 30 ml of 1N NaOH were added to the combined toluene phases. The basic water phase was made acidic with 3 g of conc. H2SO4 and extracted with 2×25 ml of toluene. The combined organic phases were washed 3× with H2O, dried over Na2SO4 and evaporated to dryness. 17 mmol (2.82 g) of p-methoxyphenylacetic acid (yield 68% of theory) with a purity of 98% were obtained.

Provenance & Evidence