Water → HCID 20310681, compound

HRID 259026Notes

Reaction equation

HRID 259026 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 hours the solution is cooled, filtered and evaporated to dryness. The residue is dissolved in 30 ml. of dimethylformamide and 2.48 g. (1eq.) 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 is 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. temperatureAfter 2 hours the 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-0be9ed827ac84da7a35ea3bf80411676
Source dataset
uspto-grants-1977_07
Patent number
US04035509

Reaction notes

Loading…