Aspirin → 2-Acetoxybenzoyl chloride

Temperature

80 °C

Acetyl salicylic acid (1.0 g) was mixed with thionyl chloride (1.0 mL) and mixture was heated in a 50 mL round bottom flask under nitrogen at 80° C. for 1 hour. The excess thionyl chloride was removed by distillation, dried in high vacuum to get acetyl salicyloyl chloride as a viscous liquid, ˜1.1 g. Used for next step with out further purification. Curcumin (0.50 g) was taken in 10 mL of DMF in a 50 mL round bottom flask under nitrogen and pyridine was added. Acetyl salicyloyl chloride (˜1.1 g) was taken in 5 mL of DMF and was added drop wise from a pressure equalizing separating funnel. The solution turned darker in color. The mixture was heated at 90° C. for 1 hour and then at room temperature overnight. To the reaction mixture 100 mL of water was added. A solid formed which was filtered, the solid was stirred with 30 mL of NaHCO3 solution. The solid was filtered, washed with water, dried under high vacuum to yield 1.10 g of the product, curcumin acetyl salicylate or curcumin-aspirin, NMR was consistent with the structure.

1. customThe excess thionyl chloride was removed by distillation
2. customdried in high vacuum

ORD record

ord-9df5a65348c84b4282e49c290ee2673d

Source dataset

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09012411B2