Aluminum(III) Chloride → HCID 15480072, compound

HRID 1872854Notes

Reaction equation

HRID 1872854 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[Br:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH2:14][C:15](O)([CH3:17])[CH3:16])=[C:8]([C:19]([CH3:22])([CH3:21])[CH3:20])[CH:7]=1>[N+](C)([O-])=O>[Br:5][C:6]1[CH:7]=[C:8]([C:19]([CH3:22])([CH3:21])[CH3:20])[C:9]2[O:12][CH2:13][CH2:14][C:15]([CH3:17])([CH3:16])[C:10]=2[CH:11]=1

Participants

4

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 10495522HCID 10495522, compound

Product 1

HCID 15480072HCID 15480072, compoundYield 77.2%

Reagents, catalysts & solvents 1

HCID 6375NitromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a cold (0° C.) suspension of AlCl3 (1.67 g, 12.51 mmol, 1 equiv) in nitromethane (20 mL) is added a solution of 4-bromo-2-tert-butyl-1-(3-hydroxy-3-methylbutoxy)benzene (3.94 g, 12.51 mmol) in nitromethane (5 mL). The resulting red solution is stirred at 0° C. After 1 h, the reaction mixture is quenched by slow addition of water, diluted with hexanes, and washed with water and brine. The aqueous layers are extracted with hexanes; the combined organic layers are dried (MgSO4), filtered and concentrated. The residue is purified by flash column chromatography on silica (hexanes) to give the title compound (2.87 g, 77%) as a solid which is recrystallized using hexanes to give white crystals.

Workup

  1. customthe reaction mixture is quenched by slow addition of water
  2. additiondiluted with hexanes
  3. washwashed with water and brine
  4. extractionThe aqueous layers are extracted with hexanes
  5. dry with materialthe combined organic layers are dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue is purified by flash column chromatography on silica (hexanes)

Sources & evidence

ORD record
ord-04459d02d5714e1ba42e46c26998a14b
Source dataset
uspto-grants-2000_08
Patent number
US06110960

Reaction notes

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