Acetic Anhydride → Oxacyclotridecane-2,13-dione

A starting mixture of 23 gms (0.1 mole) of 1,10-decanedicarboxylic acid and 18 gms (0.1 mole) of acetic anhydride was refluxed for 18 hours and then concentrated in vacuo to remove acetic acid and excess acetic anhydride. The residue was dissolved in 300 ml methylene chloride, filtered, washed with ice-cold 5% sodium bicarbonate solution, water, and saturated sodium chloride. After the final separation of the layers, the organic solution was dried over MgSO4, filtered, and evaporated in vacuo to give 20 gms crude product. This was purified by dissolving it in 100 ml boiling methylene chloride, filtering hot, diluting with 200 ml hexanes, and refrigerating. This resulted in 13 gms pure title product m.p. 85°-9°.

1. temperaturewas refluxed for 18 hours
2. concentrationconcentrated in vacuo
3. customto remove acetic acid and excess acetic anhydride
4. dissolutionThe residue was dissolved in 300 ml methylene chloride
5. filtrationfiltered
6. washwashed with ice-cold 5% sodium bicarbonate solution, water, and saturated sodium chloride
7. customAfter the final separation of the layers
8. dry with materialthe organic solution was dried over MgSO4
9. filtrationfiltered
10. customevaporated in vacuo
11. customto give 20 gms crude product
12. customThis was purified
13. dissolutionby dissolving it in 100 ml
14. filtrationfiltering hot
15. additiondiluting with 200 ml hexanes

ORD record

ord-ce2b3cd5120a4656976d053f2806e889

Source dataset

uspto-grants-1989_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04861798