2-prop-2-enylbutanedioic acid

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Water (321 g, 321 mL, 1.78 moles) was placed in a 1 L, 3-neck RBF and briefly vacuumed to remove oxygen. Then allyl succinic anhydride (50 g, 42.7 mL, 357 mmoles) was added and the reaction solution heated to 110 C overnight. The reaction solution was then cooled to room temperature and the volatiles removed from a sample to prepare for FTIR analysis. After confirming the anhydride had been converted to carboxylic acid, the volatiles were removed by vacuum transfer while stirring the reaction solution at 30 C. The reaction flask temperature was maintained with a temperature controller while being monitored using a thin wire thermocouple placed between the heating mantle and reaction flask. As the product began to solidify, the solids were broken up to facilitate drying. After the majority of the water had been removed, the flask was connected directly to the Schlenk line to achieve a pressure <20 mtorr overnight. The product is a white solid (55.6 g, 352 mmoles, 98.5% yield). 1H NMR (DMSO-d6, δ): 2.07 to 2.35 and 2.42 to 2.52 (m, 4H, CH2═CHCH2CH(CO2H)CH2CO2H), 2.66 to 2.74 (m, 1H, CH2CH(CO2H)CH2), 5.00 to 5.09 (m, 2H, CH2═CHCH2) 5.6 to 5.78 (m, 1H, CH2═CHCH2CH). IR (cm−1, diamond): 2300 to 3700 (broad CO2H), 3029 w (sp2 C—H), 2978w, 2921w (sp3 C—H), 1689 s (C═O). to remove oxygen the reaction solution heated to 110 C overnight the volatiles removed from a sample to prepare for FTIR analysis the volatiles were removed by vacuum transfer The reaction flask temperature was maintained with a temperature controller thermocouple placed between the heating mantle and reaction flask to facilitate drying After the majority of the water had been removed a pressure <20 mtorr overnight