Water → Octyl methacrylate

Participants

Reaction Conditions

Reaction Steps

To 30.0 g (267 mmoles, 3 eq) of 1-octene was added 0.802 g (5.35 mmoles, 0.06 eq) of trifluoromethanesulfonic acid followed by 7.67 g (89.1 mmoles, 1 eq) of methacrylic acid. This mixture was heated to 90° C. for 6 hours. By NMR, the yield was 81% based on acrylic acid consumed. To the reaction mixture was added 36.16 g of a saturated solution of sodium bicarbonate in water (8.28 wt-%, 35.6 mmoles, 0.4 eq) and the mixture was stirred at room temperature for 1 hour. The aqueous phase was removed and the residue was distilled at 25° C./10-20 torr. The receiver was cooled with dry ice to trap the octene. This gave 14 grams of recovered octene. The product was distilled at 103° C./1.0 torr to give 14.7 g of octyl methacrylate (83.2% yield based on acrylic acid consumed).

Provenance & Evidence