Aluminum(III) Chloride → HCID 4438647, compound

HRID 1111275Notes

Reaction equation

HRID 1111275 reaction equation
C([C:5]1[C:6]([OH:20])=[C:7]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[OH:19])[CH:8]=[C:9]([CH3:11])[CH:10]=1)(C)(C)C.[Cl-].[Al+3].[Cl-].[Cl-]>C1C=CC=CC=1>[OH:20][C:6]1[CH:5]=[CH:10][C:9]([CH3:11])=[CH:8][C:7]=1[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[OH:19]

Participants

4

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 22151948HCID 22151948, compound

Product 1

HCID 4438647HCID 4438647, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

(3-t-Butyl-2-hydroxy-5-methylphenyl)-(2-hydroxyphenyl)methane (4.34 g, 16 mmol) was combined with 3.2 g (24 mmol) of aluminum chloride and 100 ml of benzene and the mixture heated at reflux with stirring for 24 hours. It was then allowed to cool and was poured onto an ice-water mixture. The organic phase was collected and extracted with water and then 1N potassium hydroxide. The alkaline extract was acidified and then extracted with ether. The ether extract was dried with magnesium sulfate and the volatiles removed by evaporation under reduced pressure to obtain 1.66 g (48 percent of theory) of the title compound as an oil. The proton nmr spectrum was consistent with the assigned structure.

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux
  3. temperatureto cool
  4. customThe organic phase was collected
  5. extractionextracted with water
  6. extractionThe alkaline extract
  7. extractionextracted with ether
  8. extractionThe ether extract
  9. dry with materialwas dried with magnesium sulfate
  10. customthe volatiles removed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-753c9ed479584c84a0f1562c34013177
Source dataset
uspto-grants-1990_12
Patent number
US04979978

Reaction notes

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