Water → HCID 20310681, compound

HRID 1283668Notes

Reaction equation

HRID 1283668 reaction equation
C(Cl)(Cl)(Cl)Cl.BrN1C(=[O:12])CCC1=O.[C:14]1([C:23]2[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH:24]=2)[CH2:22][CH2:21][CH2:20][CH2:19]CCNN=1.O.[C:33]([O:36][CH2:37]C)(=[O:35])[CH3:34]>>[C:33]([C:34]1[CH:19]=[CH:20][C:21]2[C:22](=[O:12])[C:14]3[CH:23]=[CH:31][CH:30]=[CH:29][C:28]=3[CH:27]=[CH:26][C:25]=2[CH:24]=1)([O:36][CH3:37])=[O:35]

Participants

6

Reactant 5

HCID 962WaterHCID 5943Carbon TetrachlorideHCID 8857Ethyl AcetateHCID 67184N-bromobutanimideHCID 66586414Diazabicylononene

Product 1

HCID 20310681HCID 20310681, compound

Conditions

Temperature
60 °C

Procedure

4.68 G. of 2-carbomethoxy-5-oxo-5H-dibenzo[a,d] cycloheptane is refluxed in 100 ml. of carbon tetrachloride containing 3.56 g. (1 eq.) of N-bromosuccinimide while being irradiated with a 100 watt incandescent lamp. After 2 hrs. the solution is cooled, filtered and evaporated to dryness. The residue is dissolved in 30 ml. of dimethylformamide and 2.48 g. (1 eq.) of diazabicylononene is added. The mixture is heated briefly to 60° C, and water and ethyl acetate are added. The organic layer is washed with dilute hydrochloric acid and water, then dried and evaporated to give 2-carbomethoxy-5-oxo-5H-dibenzo[a,d]cycloheptene. Hydrolysis in eight to one aqueous methanol, 5% potassium hydroxide, followed by acidification with dilute hydrochloric acid yields 5-oxo-5H-dibenzo[a,d] -cycloheptene-2-carboxylic acid (m.p. 261°-262°C).

Workup

  1. temperaturethe solution is cooled
  2. filtrationfiltered
  3. customevaporated to dryness
  4. dissolutionThe residue is dissolved in 30 ml
  5. washThe organic layer is washed with dilute hydrochloric acid and water
  6. customdried
  7. customevaporated

Sources & evidence

ORD record
ord-c83c01648914499ebbfc7f1065b37a3d
Source dataset
uspto-grants-1976_08
Patent number
US03975540

Reaction notes

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