Acetate → HCID 12690627, compound

HRID 1730973Notes

Reaction equation

HRID 1730973 reaction equation
[CH:1]1[C:11]2[CH:10]=[CH:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[C:6](=[O:16])[C:5]=2[CH:4]=[CH:3][CH:2]=1.Br[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20].C([O-])(=O)C>[Zn].C1C=CC=CC=1>[CH2:22]([O:21][C:19](=[O:20])[CH2:18][C:6]1([OH:16])[C:7]2[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=2[CH:9]=[CH:10][C:11]2[CH:1]=[CH:2][CH:3]=[CH:4][C:5]1=2)[CH3:23]

Participants

6

Reactant 3

HCID 175AcetateHCID 7748Ethyl bromoacetateHCID 166795H-Dibenzo[a,d]cyclohepten-5-one

Product 1

HCID 12690627HCID 12690627, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 241BenzeneSolvent2×

Procedure

To a suspension of 8.35 g. of activated zinc in 120 ml. of absolute benzene is added at room temperature a solution of 10.3 g. of dibenzo[a,d]cyclohepten-5-one and 8.35 g. of ethyl bromoacetate in 50 ml. of absolute benzene. After about one quarter of said solution has been so added the mixture is heated at reflux until the resulting reaction subsides and then the remainder of the solution is added while maintaining reflux temperatures. After addition is completed the resulting mixture is refluxed for an additional 4 hours. The resulting mixture is then added to dilute acetate acid and extracted 2 times with ethyl acetate. The combined organic phases are washed with water, dried and evaporated in vacuo. The residue is crystallized from diethyl ether/pentane to obtain 5-hydroxy-dibenzo[a,d]cyclohepten-5-acetic acid ethyl ester, m.p. 93°-99° C.

Workup

  1. additionTo a suspension of 8.35 g
  2. additionAfter about one quarter of said solution has been so added the mixture
  3. temperatureis heated
  4. temperatureat reflux until the resulting reaction subsides
  5. additionthe remainder of the solution is added
  6. temperaturewhile maintaining
  7. temperaturereflux temperatures
  8. additionAfter addition
  9. temperatureis refluxed for an additional 4 hours
  10. extractionextracted 2 times with ethyl acetate
  11. washThe combined organic phases are washed with water
  12. customdried
  13. customevaporated in vacuo
  14. customThe residue is crystallized from diethyl ether/pentane

Sources & evidence

ORD record
ord-89488cf4c33e42c3b5469afa5c501b5c
Source dataset
uspto-grants-1976_11
Patent number
US03994918

Reaction notes

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