Hydrochloric Acid → HCID 12569784, compound

HRID 1154927Notes

Reaction equation

HRID 1154927 reaction equation
[N+](=[CH:3][C:4](=[O:24])[CH2:5][CH2:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH2:17][CH2:18][C:19](=[O:23])[CH:20]=[N+]=[N-])=[CH:11][CH:10]=1)=[N-].[Cl-:25].[Na+].[ClH:27].O>CO>[Cl:25][CH2:3][C:4](=[O:24])[CH2:5][CH2:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH2:17][CH2:18][C:19](=[O:23])[CH2:20][Cl:27])=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 5234Sodium ChlorideHCID 53695609HCID 53695609, compound

Product 1

HCID 12569784HCID 12569784, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of about 27 millimoles of 1,4-bis-(6'-diazo-5'-oxohexyl)-benzene (prepared from 7.6 g of p-phenylene-δ,δ-divaleryl chloride) in 70 ml of methanol is added dropwise to a mixture of 58 ml of 5 M aqueous sodium chloride solution and 58 ml of 2 N aqueous hydrochloric acid solution. During the dropwise addition, the material in the reaction vessel must be cooled and stirred vigorously. After the addition, and when nitrogen evolution has ceased, stirring is continued for 4 hours at room temperature. 200 ml of water are added to the solution and the mixture is extracted with chloroform. The combined chloroform phases are washed with 200 ml of water and the pale yellow solution is dried over sodium sulfate. It is then filtered and concentrated on a rotary evaporator. The yellow solid residue is chromatographed on a silica gel column (length 50 cm, diameter 5 cm), using chloroform as the mobile phase. The bis-chloroketone migrates fastest. After concentrating the fractions, colorless 1,4-bis-(6'-chloro- 5'-oxohexyl)-benzene is obtained, and this is recrystallized from cyclohexane. The substance is obtained in 53% yield (4.9 g); melting point 86°-87° C.

Workup

  1. additionDuring the dropwise addition
  2. temperaturethe material in the reaction vessel must be cooled
  3. additionAfter the addition, and when nitrogen evolution
  4. stirringstirring
  5. extractionthe mixture is extracted with chloroform
  6. washThe combined chloroform phases are washed with 200 ml of water
  7. dry with materialthe pale yellow solution is dried over sodium sulfate
  8. filtrationIt is then filtered
  9. concentrationconcentrated on a rotary evaporator
  10. customThe yellow solid residue is chromatographed on a silica gel column (length 50 cm, diameter 5 cm)
  11. concentrationAfter concentrating the fractions

Sources & evidence

ORD record
ord-d396aef2abfa4c8381dfd234d0712e67
Source dataset
uspto-grants-1981_11
Patent number
US04298751

Reaction notes

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