Chloroform → HCID 20310684, compound
Reaction equation
[O:1]=[C:2]1[C:8]2[CH:9]=[CH:10][C:11]([C:13](O)=[O:14])=[CH:12][C:7]=2[CH:6]=[CH:5][C:4]2[CH:16]=[CH:17][CH:18]=[CH:19][C:3]1=2.C(Cl)(Cl)[Cl:21].S(Cl)(Cl)=O>CN(C)C=O>[Cl:21][C:13]([C:11]1[CH:10]=[CH:9][C:8]2[C:2](=[O:1])[C:3]3[CH:19]=[CH:18][CH:17]=[CH:16][C:4]=3[CH:5]=[CH:6][C:7]=2[CH:12]=1)=[O:14]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
22 G. of 5-oxo-5H-dibenzo[a,d]cycloheptene-2-carboxylic acid is stirred in 200 ml. of chloroform, 50 ml. of thionyl chloride and 1 ml. of dimethylformamide for 8 hours. The mixture is evaporated to dryness and the residue recrystallized from acetonitrile to yield 2-chloroformyl-5-oxo-5H-dibenzo[a,d]cycloheptene. This is dissolved in 200 ml. of chloroform and added to a 3-fold excess of ethereal diazomethane at 0° C. The mixture is left at 0° C for 12 hrs. then evaporated to dryness. The residue is recrystallized from acetonitrile to yield 2-diazoacetyl-5-oxo-5H-dibenzo[a,d]cycloheptene. The diazoketone is heated to reflux in 250 ml. of ethanol and a saturated triethylamine solution of 2 g. of silver benzoate is added slowly until gas evolution ceases. The solution is cooled, filtered and evaporated to yield ethyl (5-oxo-5H-dibenzo[a,d]cyclohepten-2-yl)acetate. This ester is refluxed in 5% aqueous potassium hydroxide for 12 hrs. The solution is cooled, acidified with dilute hydrochloric acid and extracted with ether. The ether extract is dried and evaporated to yield (5-oxo-5H-dibenzo[a,d]cyclohepten-2-yl)acetic acid which can be recrystallized from acetone-hexane.
Workup
- customThe mixture is evaporated to dryness
- customthe residue recrystallized from acetonitrile
Sources & evidence
- ORD record
- ord-5c3f8c62f1b6444b84ee79e404e2076d
- Source dataset
- uspto-grants-1978_09
- Patent number
- US04112114
Reaction notes
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