2-(2-Hydroxyphenoxy)benzoic acid → 11H-Dibenzo(b,e)(1,4)dioxepin-11-one

HRID 1692638Notes

Reaction equation

HRID 1692638 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 1

HCID 6113882-(2-Hydroxyphenoxy)benzoic acid

Product 1

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

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
146.5 °C

Procedure

2-(2-Hydroxy-phenoxy)-benzoic acid (200 mg) was dissolved in acetic anhydride (10 ml) and refluxed at 145-148° C. for 8 h. The excess acetic anhydride was evaporated by a rotatory evaporator and the residue was poured into ice water. The mixture was extracted with diethyl ether. The organic layer was successively washed with saturated NaHCO3 and saturated ammonium chloride, dried over anhydrous MgSO4, filtered and evaporated by a rotatory evaporator. After dryness and purification by column chromatography, the final product was provided.

Workup

  1. customThe excess acetic anhydride was evaporated by a rotatory evaporator
  2. additionthe residue was poured into ice water
  3. extractionThe mixture was extracted with diethyl ether
  4. washThe organic layer was successively washed with saturated NaHCO3 and saturated ammonium chloride
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationfiltered
  7. customevaporated by a rotatory evaporator
  8. customAfter dryness and purification by column chromatography

Sources & evidence

ORD record
ord-d34274d34e13422294c29dea65c8c82e
Source dataset
uspto-grants-2012_04
Patent number
US08158623B2

Reaction notes

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