Hydrochloric Acid → HCID 20306107, compound

HRID 1732395Notes

Reaction equation

HRID 1732395 reaction equation
[C:1](Cl)(=[O:6])[CH2:2][CH2:3][CH2:4][CH3:5].Cl[C:9]1[CH:14]=[CH:13][CH:12]=[C:11](Cl)[CH:10]=1.[Cl-:16].[Al+3].[Cl-:18].[Cl-].Cl>O>[Cl:16][CH:2]([CH2:3][CH:4]([Cl:18])[CH3:5])[C:1]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:6]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 109431,3-DichlorobenzeneHCID 61186Valeryl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 20306107HCID 20306107, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 48.0 g. (0.398 mole) of valeryl chloride in 100.0 g. (0.680 mole) of m-dichlorobenzene is added portionwise at less than 5°, 66.7 g. (0.5 mole) of aluminum chloride. When the addition is complete, the reaction mixture is allowed to stir and slowly warm up to ambient temperature for 2 hours. It is then heated at reflux for 3 hours, and stirred at room temperature for 16 hours. The reaction mixture is poured into iced water, and made acidic with hydrochloric acid. The oil which formed separates, and the aqueous phase is extracted twice with 200 ml. of ether. The oil and the extracts are combined, washed with water, dried and concentrated to give 122.2 g. of the crude product. A distillation (89°-93°/0.05 mm) gives 55.2 g. (60%) of the product.

Workup

  1. additionWhen the addition
  2. temperatureIt is then heated
  3. temperatureat reflux for 3 hours
  4. stirringstirred at room temperature for 16 hours
  5. customThe oil which formed separates
  6. extractionthe aqueous phase is extracted twice with 200 ml
  7. washwashed with water
  8. customdried
  9. concentrationconcentrated
  10. customto give 122.2 g
  11. distillationA distillation (89°-93°/0.05 mm)
  12. customgives 55.2 g

Sources & evidence

ORD record
ord-45887d0899364acbbe918a2ba0895380
Source dataset
uspto-grants-1980_12
Patent number
US04237158

Reaction notes

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