Acetic Acid → 6,11-Dihydro-11-ethylidenedibenz[b,e]oxepin-2-carboxylic Acid

HRID 894222Notes

Reaction equation

HRID 894222 reaction equation
C(C1[CH:19]=[CH:18][C:6]2[O:7][CH2:8][C:9]3[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=3[C:11](=[CH:12][CH3:13])[C:5]=2[CH:4]=1)#N.[C:20]([OH:23])(=[O:22])[CH3:21].Cl>O>[CH:12](=[C:11]1[C:10]2[CH:14]=[CH:15][CH:16]=[CH:17][C:9]=2[CH2:8][O:7][C:6]2[CH:18]=[CH:19][C:21]([C:20]([OH:23])=[O:22])=[CH:4][C:5]1=2)[CH3:13]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 536734252-Cyano-6,11-dihydro-11-ethylidenedibenz[b,e]oxepin

Product 1

HCID 545396956,11-Dihydro-11-ethylidenedibenz[b,e]oxepin-2-carboxylic Acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Reflux a mixture of 2.8 gm of the nitrile of Step A, 50 ml of acetic acid, 5 ml of water and 5 ml of concentrated hydrochloric acid for 140 hours. Cool the reaction mixture, separate the solids by filtration and dry. Recrystallize from toluene to obtain the title product.

Workup

  1. temperatureReflux
  2. temperatureCool the reaction mixture
  3. customseparate the solids
  4. filtrationby filtration
  5. customdry
  6. customRecrystallize from toluene

Sources & evidence

ORD record
ord-e65d07c7de3d4a0dbf28170e3b422d46
Source dataset
uspto-grants-1981_08
Patent number
US04282365

Reaction notes

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