Dibenzofuran → HCID 12331793, compound

HRID 614853Notes

Reaction equation

HRID 614853 reaction equation
[CH:1]1[C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[O:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[Cl:14][CH2:15][CH2:16][CH2:17][C:18](Cl)=[O:19].[Cl-:21].[Al+3].[Cl-].[Cl-]>C(Cl)Cl>[Cl:14][CH2:15][CH2:16][CH2:17][C:18]([C:2]1[CH:3]=[CH:4][C:5]2[O:6][C:7]3[CH:13]=[CH:12][C:11]([C:5](=[O:6])[CH2:4][CH2:3][CH2:2][Cl:21])=[CH:10][C:8]=3[C:9]=2[CH:1]=1)=[O:19]

Participants

5

Reactant 3

HCID 568DibenzofuranHCID 783704-Chlorobutyryl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 12331793HCID 12331793, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 30 g (0.18 mole) of dibenzofuran and 62.7 g (0.44 mole) of 4-chlorobutyryl chloride in 1.0 l. of dry methylene chloride previously cooled to -10° C. was added portionwise 49.9 g (0.37 mole) of aluminum chloride with stirring. When the addition was complete the reaction mixture was heated at reflux for 2 hours then stirred at room temperature for an additional 12 hours. The reaction mixture was decomposed with ice water/HCl to give the desired product which was recrystallized from isopropyl alcohol. M.P. 102°-104° C., λmaxCHCl3 252, Elcm1% 1790.

Workup

  1. additionWhen the addition
  2. temperaturewas heated
  3. temperatureat reflux for 2 hours
  4. stirringthen stirred at room temperature for an additional 12 hours

Sources & evidence

ORD record
ord-27ced1c4b5dd44dd851eb9a136779f00
Source dataset
uspto-grants-1979_03
Patent number
US04146624

Reaction notes

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