Sulfuric Acid → Benzene, 1-methyl-4-[1-(chloromethyl)-1-methylethyl]

HRID 223114Notes

Reaction equation

HRID 223114 reaction equation
[CH2:1]([Cl:5])[C:2](=[CH2:4])[CH3:3].S(=O)(=O)(O)O.[C:11]1([CH3:17])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>>[CH3:4][C:2]([C:14]1[CH:15]=[CH:16][C:11]([CH3:17])=[CH:12][CH:13]=1)([CH3:3])[CH2:1][Cl:5]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 1140TolueneHCID 112413-Chloro-2-methyl-1-propene

Product 1

HCID 524329Benzene, 1-methyl-4-[1-(chloromethyl)-1-methylethyl]Yield 85%

Procedure

24 g Methallyl chloride is added to a mixture of 92 g toluene and 49 g concentrated sulphuric acid, keeping the temperature at 40° C. No exothermal reaction occurs. Subsequently the reaction mixture is stirred during half an hour, after which the layers are separated. The organic layer is washed neutral with soda solution, dried on MgSO4 and evaporated. The residue is distilled under diminished pressure to obtain 2-methyl-2-(p-tolyl)-propyl chloride (p-methyl-neophyl chloride) in a yield of 85%.

Workup

  1. customat 40° C
  2. customNo exothermal reaction
  3. customafter which the layers are separated
  4. washThe organic layer is washed neutral with soda solution
  5. customdried on MgSO4
  6. customevaporated
  7. distillationThe residue is distilled under diminished pressure

Sources & evidence

ORD record
ord-ffca0aac55ea4cc9b8da7f6f473e096d
Source dataset
uspto-grants-1982_10
Patent number
US04352748

Reaction notes

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