TO To DT a NN-MIXTURE mixture IN-OF of CD-ALPHANUM 124E -LRB- ( CD 1.97 NN-MASS g COMMA , CD 9.0 NN-AMOUNT mmol -RRB- ) CC and OSCAR-CM sodium OSCAR-CM iodide -LRB- ( CD 0.27 NN-MASS g COMMA , CD 1.8 NN-AMOUNT mmol -RRB- ) IN-IN in CD 70 NN-PERCENT % OSCAR-CM H2SO4 -LRB- ( CD 30 NN-VOL mL -RRB- ) IN at CD 110 NN-TEMP °C IN-UNDER under OSCAR-CM nitrogen VBD was VB-ADD added OSCAR-CM acrolein -LRB- ( CD 1.1 NN-VOL mL COMMA , CD 13.6 NN-AMOUNT mmol -RRB- ) IN-VIA via NN-APPARATUS syringe NN pump -LRB- ( CD 1 NN-TIME mL/h -RRB- ) STOP . DT-THE The NN-CHEMENTITY reaction VBD was VB-STIR stirred IN-FOR for DT another CD 30 NN-TIME min IN at CD 110 NN-TEMP °C IN-AFTER after JJ complete NN-ADD addition STOP . IN-AFTER After VB-COOL cooling TO to NN-TEMP room NN-TEMP temperature COMMA , DT-THE the JJ-CHEM reaction NN-CHEMENTITY mixture VBD was VB-DILUTE diluted IN-WITH with NN-CHEMENTITY ice OSCAR-CM water -LRB- ( CD 50 NN-VOL mL -RRB- ) RB-CONJ then VB-ADD added TO to DT an OSCAR-CJ aqueous NN-CHEMENTITY solution -LRB- ( CD 500 NN-VOL mL -RRB- ) IN-OF of OSCAR-CM Na2CO3 -LRB- ( CD 60 NN-MASS g -RRB- ) RB slowly STOP . DT This NN-CHEMENTITY mixture VBD was VB-EXTRACT extracted IN-WITH with OSCAR-CM chloroform -LRB- ( CD 3x200 NN-VOL mL -RRB- ) STOP . DT-THE The JJ-CHEM combined JJ-CHEM organic NN-CHEMENTITY phases VBD were VB-DRY dried IN-OVER over OSCAR-CM Na2SO4 COMMA , VB-FILTER filtered CC and VB-CONCENTRATE concentrated STOP . DT-THE The NN-CHEMENTITY residue VBD was VB-PURIFY purified IN-BY by VB-DEGASS flush NN-CHROMATOGRAPHY chromatography -LRB- ( OSCAR-CM hexanes DASH / OSCAR-CM ethyl OSCAR-CM acetate -RRB- ) TO to VB-YIELD give CD-ALPHANUM 124F IN-AS as DT a NN-STATE solid STOP .