Trifluoroacetic anhydride → 3-(6,11-Dihydro-11-oxodibenz[b,e]oxepin-2-yl)-2,2-dimethyl-propanoic acid

HRID 357264Notes

Reaction equation

HRID 357264 reaction equation
[C:1]([C:4]([CH3:24])([CH3:23])[CH2:5][C:6]1[CH:22]=[CH:21][C:9]([O:10][CH2:11][C:12]2[CH:20]=[CH:19][CH:18]=[CH:17][C:13]=2[C:14](O)=[O:15])=[CH:8][CH:7]=1)([OH:3])=[O:2].FC(F)(F)C(OC(=O)C(F)(F)F)=O>ClCCl>[O:15]=[C:14]1[C:13]2[CH:17]=[CH:18][CH:19]=[CH:20][C:12]=2[CH2:11][O:10][C:9]2[CH:8]=[CH:7][C:6]([CH2:5][C:4]([CH3:24])([CH3:23])[C:1]([OH:3])=[O:2])=[CH:22][C:21]1=2

Participants

4

Reactant 2

HCID 9845Trifluoroacetic anhydrideHCID 675986322-[4-(2-Carboxy-2-methylpropyl)phenoxymethyl]benzoic acid

Product 1

HCID 157831793-(6,11-Dihydro-11-oxodibenz[b,e]oxepin-2-yl)-2,2-dimethyl-propanoic acidYield 19.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A slurry of 2-[4-(2-carboxy-2-methylpropyl)phenoxymethyl]benzoic acid (15.9 g) it 200 ml dry dichloromethane was treated dropwise with 12.5 ml trifluoroacetic anhydride the heated to reflux for 5 hours. Evaporation left an oil which was purified by HPLC (20:1 dichloromethane-methanol) to give 2.95 g of 3-(6,11-dihydro-11-oxodibenz[b,e]oxepin-2-yl)-2,2-dimethyl-propanoic acid a solid.

Workup

  1. temperatureheated
  2. temperatureto reflux for 5 hours
  3. customEvaporation
  4. waitleft an oil which
  5. customwas purified by HPLC (20:1 dichloromethane-methanol)

Sources & evidence

ORD record
ord-14389d902d7941dba6068a7453e3cc4b
Source dataset
uspto-grants-1998_11
Patent number
US05840749

Reaction notes

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