Acetic Anhydride → 11H-Dibenzo(b,e)(1,4)dioxepin-11-one

HRID 1462183Notes

Reaction equation

HRID 1462183 reaction equation
O[C:2]1[CH:17]=[CH:16][CH:15]=[CH:14][C:3]=1[O:4][C:5]1[CH:13]=[CH:12][CH:11]=[CH:10][C:6]=1[C:7]([OH:9])=[O:8].C(OC(=O)C)(=O)C>>[CH:10]1[C:6]2[C:7](=[O:9])[O:8][C:2]3[CH:17]=[CH:16][CH:15]=[CH:14][C:3]=3[O:4][C:5]=2[CH:13]=[CH:12][CH:11]=1

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 6113882-(2-Hydroxyphenoxy)benzoic acid

Product 1

HCID 6512311H-Dibenzo(b,e)(1,4)dioxepin-11-one

Procedure

5.06 g of 2-(2-hydroxyphenoxy) benzoic acid were suspended in 35 ml of newly distilled acetic anhydride, then the mixture was refluxed for 3 hours while the reaction is controlled from time to time by analyzing a sample of the mixture by gas chromatography. The excess of acetic anhydride was then removed by distillation under reduced pressure and the oily residue crystallized at rest. The crystals were left overnight in a refrigerator; then they were taken up with some ml of ether. The crystalline mass was filtered off, squeezed out, rinsed with some ml of ether and dried under vacuum. The obtained dibenzo (b,e) dioxepinone was purified on fractional distillation under reduced pressure. The pure product distills over at 0.01 mmHg, and melts at 62°-66° C.

Workup

  1. temperaturethe mixture was refluxed for 3 hours while the reaction
  2. customThe excess of acetic anhydride was then removed by distillation under reduced pressure
  3. customthe oily residue crystallized at rest
  4. filtrationThe crystalline mass was filtered off
  5. washrinsed with some ml of ether
  6. customdried under vacuum
  7. distillationThe obtained dibenzo (b,e) dioxepinone was purified on fractional distillation under reduced pressure
  8. distillationThe pure product distills over at 0.01 mmHg, and melts at 62°-66° C.

Sources & evidence

ORD record
ord-e8fbc42b1c154820a5a23028392c7f4e
Source dataset
uspto-grants-1984_07
Patent number
US04459306

Reaction notes

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