Benzene → HCID 53698876, compound

HRID 2397648Notes

Reaction equation

HRID 2397648 reaction equation
[CH2:1]([O:3][C:4](=[O:20])[CH2:5][CH:6]1[CH2:19][C:10]2[O:11][C:12]3[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=3[C:9]=2[CH2:8][CH2:7]1)[CH3:2].ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl.C1C=CC=CC=1>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:20])[CH2:5][C:6]1[CH:7]=[CH:8][C:9]2[C:13]3[CH:14]=[C:15]([Cl:18])[CH:16]=[CH:17][C:12]=3[O:11][C:10]=2[CH:19]=1)[CH3:2]

Participants

5

Reactant 3

HCID 241BenzeneHCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 54248074HCID 54248074, compound

Product 1

HCID 53698876HCID 53698876, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 7.23 g. of 8-chloro-1,2-dihydro-3(4H)-dibenzofuranacetic acid ethyl ester, 11.8 g. of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone and 150 ml. of benzene was stirred at reflux temperature for 18 hours under an atmosphere of nitrogen, and then cooled. The solid was removed by filtration and washed with benzene. The filtrate and washings were combined and concentrated under reduced pressure to yield 14.1 g. of dark oil, which was dissolved in methylene chloride and filtered through 143.5 g. of alumina II (neutral) in a column 60 mm. in width and 65 mm. in lenght. The eluate was evaporated to 3.28 g. of yellowish solid, which was crystallized first from a mixutre of ether-pentane, and then from ether alone to give 1.35 g. of 8-chloro-'-dibenzofuranacetic acid ethyl ester having a melting point of 90°-91°.

Workup

  1. additionA mixture of 7.23 g
  2. temperatureat reflux temperature for 18 hours under an atmosphere of nitrogen
  3. temperaturecooled
  4. customThe solid was removed by filtration
  5. washwashed with benzene
  6. concentrationconcentrated under reduced pressure
  7. customto yield 14.1 g
  8. filtrationfiltered through 143.5 g
  9. customThe eluate was evaporated to 3.28 g
  10. customof yellowish solid, which was crystallized first from a mixutre of ether-pentane
  11. customfrom ether alone to give 1.35 g

Sources & evidence

ORD record
ord-dab3aa6ce6b34d8e9849ac8d2da58565
Source dataset
uspto-grants-1977_05
Patent number
US04022805

Reaction notes

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