Acetic acid 10-acetoxymethyl-anthracen-9-ylmethyl ester → HCID 13654799, compound

Temperature

110 °C

Concentrated sulfuric acid (two drops) was added to a solution of 2,3-dimethyl-4-(2,2,3,3-tetrafluoropropoxy)pyridine-1-oxide (2.6 g) in acetic anydride (8 ml). The mixture was stirred at 110° C. for 4 hours, which was then concentrated. The residue was dissolved in methanol (20 ml), to which was added sodium hydroxide (1.2 g) dissolved in water (5 ml). The mixture was stirred at room temperature for 30 minutes, which was concentrated. To the residue was added water, and the mixture was subjected to extraction with ethyl acetate. The extract was dried on magnesium sulfate, followed by removal of the solvent by evaporation. The residue was chromatographed on a column of silica gel (50 g), eluted with chloroform-methanol (10:1), and recrystallized from isopropyl ether to yield 1.6 g of 2-hydroxymethyl-3-methyl-4-(2,2,3,3-tetrafluoropropoxy)pyridine as yellow crystals, m.p. 67°-68° C.

1. concentrationwhich was then concentrated
2. dissolutionThe residue was dissolved in methanol (20 ml), to which
3. additionwas added sodium hydroxide (1.2 g)
4. dissolutiondissolved in water (5 ml)
5. stirringThe mixture was stirred at room temperature for 30 minutes
6. concentrationwhich was concentrated
7. additionTo the residue was added water
8. extractionthe mixture was subjected to extraction with ethyl acetate
9. customThe extract was dried on magnesium sulfate
10. customfollowed by removal of the solvent by evaporation
11. customThe residue was chromatographed on a column of silica gel (50 g)
12. washeluted with chloroform-methanol (10:1)
13. customrecrystallized from isopropyl ether

ORD record

ord-3385d19c944a4f86b62403eb7a76a7a4

Source dataset

uspto-grants-1987_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04689333