Toluene → Methyl 3-methoxy-2-oxocyclopentane-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

1.38 g of sodium metal was added to 100 ml of toluene, and the mixture was heated to 60° C. 10.2 g of dimethyl α-methoxyadipate [prepared as described in step (a) above] were then added dropwise to the hot mixture. The mixture was then heated under reflux for 8 hours, after which it was cooled to room temperature and added to a 10% w/v aqueous solution of acetic acid. The organic layer was separated, washed first with a saturated aqueous solution of sodium carbonate and then with water, and then dried over anhydrous sodium sulfate. The solvent was then evaporated off under reduced pressure, and the residue was distilled, to give 4.66 g of the title compound as a pale oil, boiling at 83°-87° C./3 mm Hg (about 400 Pa).

Provenance & Evidence