Thionyl Chloride → 4,9-Bis(ethyloxy)naphtho[2,3-c]furan-1,3-dione

Participants

Reaction Conditions

Reaction Steps

1,4-Bis(ethyloxy)-2,3-naphthalenedicarboxylic acid (10.3 g, 33.8 mmol) was added to a three neck flask and chloroform (80 ml) added and stirred. Thionyl chloride (49.2 ml, 355.4 mmol) in a dropping funnel was added dropwise over 25 minutes whilst monitoring temperature (no change). The reaction was heated at relfux (65° C.) overnight. LC/MS indicated no starting material remained. Reaction mixture was cooled to room temperature and solvent evaporated. The product was azeotroped with chloroform (×2) to remove the remaining traces of thionyl chloride to give the title compound as*a pale yellow solid (9.86 g).

Provenance & Evidence