Acetic Acid → 6,11-Dihydro-11-oxodibenz[b,e]oxepin-9-carboxylic Acid

HRID 894174Notes

Reaction equation

HRID 894174 reaction equation
[O:1]=[C:2]1[C:8]2[CH:9]=C(C#N)[CH:11]=[CH:12][C:7]=2[CH2:6][O:5][C:4]2[CH:15]=[CH:16][CH:17]=[CH:18][C:3]1=2.[C:19]([OH:22])(=[O:21])[CH3:20].Cl>O>[O:1]=[C:2]1[C:8]2[CH:9]=[C:20]([C:19]([OH:22])=[O:21])[CH:11]=[CH:12][C:7]=2[CH2:6][O:5][C:4]2[CH:15]=[CH:16][CH:17]=[CH:18][C:3]1=2

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 129291409-Cyano-6,11-dihydro-11-oxodibenz[b,e]oxepin

Product 1

HCID 129291416,11-Dihydro-11-oxodibenz[b,e]oxepin-9-carboxylic Acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Reflux a mixture of 7.43 gm. (0.0316 mole) of 6,11-dihydro-11-oxodibenz[b,e]oxepin-9-carbonitrile, 130 ml. of acetic acid, 13 ml. of water and 13 ml. of concentrated hydrochloric acid for 156 hours. Cool the reaction mixture, separate the solids by filtration and dry (yield 6.20 gm., m.p. 264°-269° C.). Recrystallize from acetic acid to obtain the title product (m.p. 270.5°-271.5° C.).

Workup

  1. temperatureReflux
  2. additiona mixture of 7.43 gm
  3. temperatureCool the reaction mixture
  4. customseparate the solids
  5. filtrationby filtration
  6. customdry (yield 6.20 gm., m.p. 264°-269° C.)
  7. customRecrystallize from acetic acid

Sources & evidence

ORD record
ord-3d948dc3ebf44f6d8e59ec81c74c1bf0
Source dataset
uspto-grants-1981_08
Patent number
US04282365

Reaction notes

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