Acetoacetic Acid → 3,5-Dioxohexanoic acid

Participants

Reaction Steps

A solution of the diacetate from stage (c) (7 g) in tetrahydrofuran (150 ml) was treated with tetra-n-butylammonium fluoride (1.4 g) at room temperature for 18 h. Tlc (ether/light petroleum, 6:1) showed one major product with traces of slow moving products due to partial deacetylation. The mixture was concentrated, taken up in dry pyridine (50 ml) and treated acetic anhydride (7 ml) at room temperature for 3 h. Tlc ether/light petroleum (7:1) showed only one product. The reaction mixture was concentrated and was eluted from short column of silica gel (50 g) with ether/light petroleum (1:1) to give a crystalline product (4.3 g, 85.2%) identical with the product from Route 1, m.p. 133°-134° [α]D20 +116.3° (c 1.0, CHCl3).

Provenance & Evidence