Hydrochloric Acid → Benzene, 4-(1,1-dimethylethyl)-1,2-dimethyl-

HRID 260264Notes

Reaction equation

HRID 260264 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][C:7]=1[CH3:8].[Al+3].[Cl-].[Cl-].[Cl-].[C:13](Cl)([CH3:16])([CH3:15])[CH3:14].Cl>[OH-].[Na+].CCOCC>[C:13]([C:4]1[CH:5]=[CH:6][C:7]([CH3:8])=[C:2]([CH3:1])[CH:3]=1)([CH3:16])([CH3:15])[CH3:14]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7237O-XyleneHCID 10486tert-BUTYL CHLORIDEHCID 6451240Aluminum(III) Chloride

Product 1

HCID 81881Benzene, 4-(1,1-dimethylethyl)-1,2-dimethyl-Yield 90%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 14798Sodium HydroxideSolvent

Procedure

To o-xylene (Fluka purum, 905 ml, 7.5 mole), kept under stirring, at 0°, there was added AlCl3 (6.7 g, 50 mmole), and then, dropwise, tert-butyl chloride (Fluka puriss., 551 ml, 5 mole), during 1.25 h, while keeping the temperature between 0° and 5° (the evolving HCl was trapped in NaOH 2.5 N). The temperature was allowed to increase to room temperature. After 60 h, the reaction mixture was poured on a mixture of ice and ether, the organic phase was successively washed with brine (2x), H2O, sat. NaHCO3 and brine, dried over Na2SO4 and distilled under vacuum (Vigreux column, 30 cm) to provide 4-tert-butyl-1,2-dimethylbenzene (purity >99%, yield 90%).

Workup

  1. customthe temperature between 0° and 5°
  2. washthe organic phase was successively washed with brine (2x), H2O, sat. NaHCO3 and brine
  3. dry with materialdried over Na2SO4
  4. distillationdistilled under vacuum (Vigreux column, 30 cm)

Sources & evidence

ORD record
ord-1355806ce51b42568015bb15a3614b1d
Source dataset
uspto-grants-1996_06
Patent number
US05527769

Reaction notes

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