Acetic Anhydride → HCID 67954994, compound

Participants

Reaction Steps

Acetic anhydride (26 mL, 5 eq) was stirred together with methane sulfonyl (18 mL, 5 eq) at room temperature for 30 min and then combined with 18.0 g (55.16 mmol) of (E)-methyl 2-(2-((2,5-dimethylphenoxy)methyl)phenyl)-3-methoxyacrylate obtained in step 1 at room temperature for an additional one hour. After completion of the reaction, the reaction mixture was dropwise added to water (500 mL), adjusted to pH 7 with 25%-NaOH and extracted twice with 250 mL of dichloromethane. The organic layer was dried over anhydrous magnesium sulfate and filtered after which the solvent was removed by concentration in a vacuum. Crystallization in 100 mL of isopropyl ether (IPE) afforded 16.5 g of (E)-methyl 2-(2-((4-acetyl-2,5-dimethylphenoxy)methyl)phenyl)-3-methoxyacrylate in 81% yield as an ivory solid.

Provenance & Evidence