Diphenylmethane → 4,4'-Di-tert-butyldiphenylmethane

HRID 2066039Notes

Reaction equation

HRID 2066039 reaction equation
[C:1]1([CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:14](Cl)([CH3:17])([CH3:16])[CH3:15]>Cl.[Al+3].[Cl-].[Cl-].[Cl-]>[CH3:15][C:14]([C:4]1[CH:5]=[CH:6][C:1]([CH2:7][C:8]2[CH:9]=[CH:10][C:11]([C:1]([CH3:7])([CH3:6])[CH3:2])=[CH:12][CH:13]=2)=[CH:2][CH:3]=1)([CH3:17])[CH3:16]

Participants

5

Reactant 2

HCID 7580DiphenylmethaneHCID 10486tert-BUTYL CHLORIDE

Product 1

HCID 16527394,4'-Di-tert-butyldiphenylmethaneYield 139.8%

Reagents, catalysts & solvents 2

HCID 6451240Aluminum(III) ChlorideCatalyst2×HCID 313Hydrochloric AcidSolvent

Procedure

In a 500-ml flask, to a mixture of 16.8 g (100 mmol) of diphenylmethane and 21.3 g (230 mmol) of tert-butyl chloride, 67 mg (0.5 mmol) of anhydrous AlCl3 were added, at room temperature, under vigorous stirring, resulting in immediate HCl gas emission. The reaction mixture turned red. After 5 min, a second portion of 67 mg (0.5 mmol) of AlCl3 were added. After 5 min of vigorous stirring, the reaction mixture became hard. After about 1 h, the hard mass obtained was recrystallised from about 100 mL of hot isopropanol. The crystalline product precipitated from this solution at a temperature of −30° C. after a period of time of about 2 to 3 h. It was separated, washed with 50 ml of cold isopropanol, and dried in vacuum under a reduced pressure of 10 to 20 mm Hg. 19.6 g of product were obtained with a yield of 70%. The procedure was repeated with a yield ranging between 67 and 74%.

Workup

  1. additionwere added, at room temperature, under vigorous stirring
  2. waitAfter 5 min of vigorous stirring
  3. waitAfter about 1 h
  4. customthe hard mass obtained
  5. customwas recrystallised from about 100 mL of hot isopropanol
  6. customThe crystalline product precipitated from this solution at a temperature of −30° C. after a period of time of about 2 to 3 h
  7. customIt was separated
  8. washwashed with 50 ml of cold isopropanol
  9. customdried in vacuum under a reduced pressure of 10 to 20 mm Hg

Sources & evidence

ORD record
ord-377677bcec97417daa5609c25ab5e12c
Source dataset
uspto-grants-2012_10
Patent number
US08288602B2

Reaction notes

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