2-Chloro-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylideneacetic Acid → 2-Chloro-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylacetic Acid

HRID 67640

Reaction equation

HRID 67640 reaction equation
[Cl:1][C:2]1[CH:20]=[CH:19][C:5]2[C:6](=[CH:15][C:16]([OH:18])=[O:17])[C:7]3[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=3[CH2:9][CH2:10][C:4]=2[CH:3]=1>C(O)C.[Na].[Hg]>[Cl:1][C:2]1[CH:20]=[CH:19][C:5]2[CH:6]([CH2:15][C:16]([OH:18])=[O:17])[C:7]3[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=3[CH2:9][CH2:10][C:4]=2[CH:3]=1

Participants

4

Reactant 1

HCID 538262432-Chloro-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylideneacetic Acid

Product 1

HCID 205274972-Chloro-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylacetic Acid

Reagents, catalysts & solvents 2

HCID 9837419Sodium amalgamCatalystHCID 702EthanolSolvent

Procedure

A solution of 2-chloro-10,11-dihydro-5H-dibenzo[a,d]-cyclohepten-5-ylideneacetic acid (23.5 g, described in Example 1) in ethanol (100 ml, hot) is added to 5% sodium amalgam (100 g). The mixture is stirred at 60°-70° C. for 3 hr and decanted. The solution is evaporated of half its original volume, acidified with conc. hydrochloric acid and extracted with chloroform. The organic extract is dried and evaporated. The residue is crystallized from diethyl ether-hexane to give the title compound as crystals, mp 142°-146° C.

Workup

  1. customdecanted
  2. customThe solution is evaporated of half its original volume
  3. extractionextracted with chloroform
  4. extractionThe organic extract
  5. customis dried
  6. customevaporated
  7. customThe residue is crystallized from diethyl ether-hexane

Sources & evidence

ORD record
ord-c37440869afb46ca9a86a45406a02ba3
Source dataset
uspto-grants-1982_08
Patent number
US04346090

Linked notes

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