Acetic Anhydride → Oxacyclotridecane-2,13-dione

HRID 569107

Reaction equation

HRID 569107 reaction equation
[CH2:1]([C:14]([OH:16])=[O:15])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]([OH:13])=O.C(OC(=O)C)(=O)C>>[CH2:10]1[C:11](=[O:13])[O:16][C:14](=[O:15])[CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]1

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 12736Dodecanedioic Acid

Product 1

HCID 14098193Oxacyclotridecane-2,13-dioneYield 94.2%

Procedure

A stirred 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 13 gms pure title product m.p. 85°-9°.

Workup

  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 the organic solution
  8. dry with materialwas dried over MgSO4
  9. filtrationfiltered
  10. customevaporated in vacuo

Sources & evidence

ORD record
ord-72c38f9c8eb049ed888111a2e3a9175d
Source dataset
uspto-grants-1988_03
Patent number
US04731382

Linked notes

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