Hydrochloric Acid → 5-oxo-5H-dibenzo[a,d]cyclohepten-2-acetic acid

HRID 1576183Notes

Reaction equation

HRID 1576183 reaction equation
C1C2C=CC3C=CC=CC=3C(=O)C=2C=CC=1C(C)C#N.Cl.[CH:22]1[C:32]2[CH:31]=[CH:30][C:29]3[CH:33]=[CH:34][CH:35]=[CH:36][C:28]=3[C:27](=[O:37])[C:26]=2[CH:25]=[CH:24][C:23]=1[CH:38](C)[C:39]([OH:41])=[O:40].C1C2C=CC3C=CC=CC=3C(=O)C=2C=CC=1CC#N>CC(C)=O.CCCCCC.C(Cl)(Cl)Cl.CCCCCC.O.CCOCC.C(O)(=O)C>[CH:22]1[C:32]2[CH:31]=[CH:30][C:29]3[CH:33]=[CH:34][CH:35]=[CH:36][C:28]=3[C:27](=[O:37])[C:26]=2[CH:25]=[CH:24][C:23]=1[CH2:38][C:39]([OH:41])=[O:40]

Participants

10

Reactant 4

HCID 313Hydrochloric AcidHCID 1739105H-Dibenzo(a,d)cycloheptene-2-acetic acid, alpha-methyl-5-oxo-HCID 123988202-(5H-dibenzo[a,d]cyclohepten-5-on-2-yl)acetonitrileHCID 214030952-(5H-dibenzo[a,d]cyclohepten-5-on-2-yl)propionitrile

Product 1

HCID 123988215-oxo-5H-dibenzo[a,d]cyclohepten-2-acetic acid

Reagents, catalysts & solvents 5

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 21585165Chloroform hexaneSolventHCID 21880519Acetone hexaneSolvent

Procedure

3.4 Gm. of 2-(5H-dibenzo[a,d]cyclohepten-5-on-2-yl)propionitrile is refluxed for 90 minutes in a mixture of 210 ml. of acetic acid and 300 ml. of concentrated hydrochloric acid. The mixture is cooled and ether and water are added. The organic layer is washed, dried and evaporated to give 3.4 gm., 93%, of 2-(5H-dibenzo[a,d]cyclohepten-5-on-2-yl)propionic acid, m.p. (chloroform-hexane) 138°-139°C.; m.p. (acetone-hexane) 113°-115°C. Use of 2-(5H-dibenzo[a,d]cyclohepten-5-on-2-yl)acetonitrile gives a similar yield of 2-(5H-dibenzo[a,d]cyclohepten-5-on-2-yl)acetic acid, m.p. (acetone-hexane) 148°-149.5°C.

Workup

  1. temperatureThe mixture is cooled
  2. washThe organic layer is washed
  3. customdried
  4. customevaporated
  5. customto give 3.4 gm

Sources & evidence

ORD record
ord-fe732d2798f2444aa433e0e46c2eed80
Source dataset
uspto-grants-1976_09
Patent number
US03979430

Reaction notes

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