Trimethylhydroquinone → Diisopropyl Ether

Participants

Reaction Conditions

Reaction Steps

To 100 ml of toluene were added 2.2 g (2 mmole) of trimethylhydroquinone and 3 g (1.5 mmole) of ethyl 4-(1-hydroxyethyl)phenylacetate, and after 0.2 g of D-camphorsulfonic acid was added, the reaction solution was stirred for 18 hours with heating at 60° C., cooled and evaporated under reduced pressure. The residue was dissolved in THF, and an aqueous solution of ferric chloride was added to the solution to carry out oxidation. Isopropyl ether (IPE) was added to the reaction solution, and the mixed solution was washed with water, dried and then evaporated under reduced pressure. The crude product was purified by silica gel column chromatography using solution: IPE to give ethyl 4-[1-(3,5,6-trimethyl-1,4-benzoquinon -2-yl)ethyl]phenylacetate. Hydrolysis of this compound with 6N hydrochloric acid in THF yielded 4-[1-(3,5,6-trimethyl-1,4-benzoquinon-2-yl)ethyl]phenylacetic acid (1 g, uield of 31%). This compound was recrystallized from IPE, m.p. 142°-143° C. δ8.70(1H,COOH), 7.19(4H,s), 4.52(1H,m), 3.58(2H,s), 1.98 (9H,s), 1.57(2H,d,7Hz).

Provenance & Evidence