Hydrochloric Acid → HCID 18442573, compound

HRID 458801Notes

Reaction equation

HRID 458801 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([OH:12])=O)[CH:5]=[CH:6][C:7]=1[Cl:8].[Cl-].[Al+3].[Cl-].[Cl-].[CH3:17][O:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[O:25][CH3:26].Cl>S(Cl)(Cl)=O.ClCCl.CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([C:22]2[CH:23]=[CH:24][C:19]([O:18][CH3:17])=[C:20]([O:25][CH3:26])[CH:21]=2)=[O:12])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 7043VeratroleHCID 798743,4-Dichlorophenylacetic acidHCID 6451240Aluminum(III) Chloride

Product 1

HCID 18442573HCID 18442573, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 24386Thionyl ChlorideSolvent

Procedure

A mixture of (3,4-dichloro-phenyl)-acetic acid (11.14 g, 54.33 mmol) and anhydrous DMF (1.45 ml) in thionyl chloride (137 ml) was stirred at RT, under nitrogen, for 17 h. The excess of thionyl chloride was removed under vacuum. Anhydrous toluene was added to the residue, which was again concentrated in vacuum (repeated two more times). Powdered anhydrous aluminium chloride (11.57 g, 86.72 mmol) was added portionwise (exothermic reaction) to a stirred mixture of 1,2-dimethoxy-benzene (6.92 ml, 54.34 mmol) and the previous acyl chloride in anhydrous dichloromethane (120 ml). An exothermic reaction occurred and the reaction mixture was heated at reflux for 2 h. The reaction mixture was allowed to cool to RT and was then poured into a mixture of ice (67 g) and aqueous 7.5N HCl (64 ml). The layers were separated and the aqueous layer was extracted with dichloromethane. The combined organic extracts were washed with brine, dried over magnesium sulfate, filtered and evaporated to dryness to give a brown residue (oil and solid). After a further drying (HV), anhydrous diethylether was added and a beige solid precipitated. The beige solid was filtered and further dried (8.33 g, 47%).

Workup

  1. customThe excess of thionyl chloride was removed under vacuum
  2. additionAnhydrous toluene was added to the residue, which
  3. concentrationwas again concentrated in vacuum (repeated two more times)
  4. custom(exothermic reaction)
  5. customAn exothermic reaction
  6. temperaturethe reaction mixture was heated
  7. temperatureat reflux for 2 h
  8. temperatureto cool to RT
  9. customThe layers were separated
  10. extractionthe aqueous layer was extracted with dichloromethane
  11. washThe combined organic extracts were washed with brine
  12. dry with materialdried over magnesium sulfate
  13. filtrationfiltered
  14. customevaporated to dryness
  15. customto give a brown residue (oil and solid)
  16. dry with materialAfter a further drying (HV), anhydrous diethylether
  17. additionwas added
  18. customa beige solid precipitated
  19. filtrationThe beige solid was filtered
  20. customfurther dried (8.33 g, 47%)

Sources & evidence

ORD record
ord-cad3ebc5be304c4289b8c6a5db929606
Source dataset
uspto-grants-2007_03
Patent number
US07192950B2

Reaction notes

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