Acetic Anhydride → (+/-)-Methyl-(6-acetoxy-2, 5,7,8-tetramethylchroman-2-yl) acetate

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Reaction Steps

By the procedure of Example 6, 26.43 g. (0.10 mol.) of (±)-6-acetoxy-2-hydroxy-2,5,7,8-tetramethylchroman was reacted with trimethyl phosphonoacetate and then with 80 ml. of pyridine and 120 ml. of acetic anhydride by stirring under N 2 overnight. The solution was poured into ice-H 2 O and worked up and dried in the manner of Example 2. The crude product was filtered throgh 750 g. of 0.05-0.2 mm silica gel with 95:5 parts by volume benzene ether and then distilled to give (±)-methyl-(6-acetoxy-2, 5,7,8-tetramethylchroman-2-yl) acetate as a colorless resin: b.p. 147°-149°C./10 mmHg.

Provenance & Evidence