Aluminum(III) Chloride → HCID 68504327, compound

HRID 2241053Notes

Reaction equation

HRID 2241053 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:9])=[CH:4][C:3]=1[O:16]C.[Al+3].[Cl-].[Cl-].[Cl-]>C1(C)C=CC=CC=1>[OH:16][C:3]1[CH:4]=[C:5]([C:8]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)=[O:9])[CH:6]=[CH:7][C:2]=1[CH3:1]

Participants

4

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 21956516HCID 21956516, compound

Product 1

HCID 68504327HCID 68504327, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Compound 39 (5 g, 22.1 mmol) was combined with AlCl3 (9 g, 66.3 mmol) and anhydrous toluene (50 mL) in a 200 mL round bottom flask. The stirring mixture was refluxed for 1 h under nitrogen then cooled to ambient temperature and quenched with 1 N aqueous HCl (50 mL). The reaction was extracted with ethyl acetate (3×100 mL). The combined organic extracts were dried (MgSO4), filtered, and the solvents removed in vacuuo. The resulting residue was treated with 10% EtOAc/hexanes at which time a solid precipitated from the solvent. The solid was filtered and dried in vacuuo for 4 h to give 3.1 g (70%) of compound 40 as an ash solid. 1H NMR (400 MHz, CDCl3): δ 2.13 (s, 3H), 7.10-7.62 (m, 6H), 7.64-7.72 (m, 2H).

Workup

  1. temperatureThe stirring mixture was refluxed for 1 h under nitrogen
  2. customquenched with 1 N aqueous HCl (50 mL)
  3. extractionThe reaction was extracted with ethyl acetate (3×100 mL)
  4. dry with materialThe combined organic extracts were dried (MgSO4)
  5. filtrationfiltered
  6. customthe solvents removed in vacuuo
  7. additionThe resulting residue was treated with 10% EtOAc/hexanes at which time a solid
  8. customprecipitated from the solvent
  9. filtrationThe solid was filtered
  10. customdried in vacuuo for 4 h

Sources & evidence

ORD record
ord-e3ad8131bf7f419c87170e193c4bd46e
Source dataset
uspto-grants-2010_05
Patent number
US07723393B2

Reaction notes

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