Acetaldehyde → 1-(1-Chloroethyl)-4-(2-methylpropyl)benzene

HRID 1268413Notes

Reaction equation

HRID 1268413 reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH:2]([CH3:4])[CH3:3].[CH:11](=O)[CH3:12].[ClH:14]>[Cl-].[Zn+2].[Cl-]>[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]([Cl:14])[CH3:12])=[CH:7][CH:6]=1)[CH:2]([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 177AcetaldehydeHCID 313Hydrochloric AcidHCID 10870Isobutylbenzene2×

Product 1

HCID 30173041-(1-Chloroethyl)-4-(2-methylpropyl)benzene

Reagents, catalysts & solvents 1

HCID 3007855ZincchlorideCatalyst

Procedure

Isobutylbenzene (402 g, 3 mol) and zinc chloride (136 g, 1 mol) are fed into a one liter flask equipped with termometer, stirrer, and gas inlet tube. The reaction is maintained below 10° C. by external cooling. A mixture of acetaldehyde (44 g, 1 mol) and isobutylbenzene (67 g, 0.5 mol) are added to the flask dropwise for 2 hours while maintaining the temperature of the flask below 10° C. The reaction is heated to room temperature and HCl is passed through the reaction medium in the flask for about 2 hours. The reaction is stirred for 6 hours. The solution is quenched with water and the organic layer is separated from the aqueous layer. The organic layer is washed with sodium bicarbonate and water, and then dried. It is then stripped of isobutylbenzene and vacuum distilled to give 1-(4′-isobutylphenyl)ethyl chloride.

Workup

  1. customequipped with termometer, stirrer, and gas inlet tube
  2. temperatureThe reaction is maintained below 10° C. by external cooling
  3. additionare added to the flask dropwise for 2 hours
  4. temperaturewhile maintaining the temperature of the flask below 10° C
  5. customThe solution is quenched with water
  6. customthe organic layer is separated from the aqueous layer
  7. washThe organic layer is washed with sodium bicarbonate and water
  8. customdried
  9. distillationdistilled

Sources & evidence

ORD record
ord-0b18df2bd7c14edc82ce41840a621aa1
Source dataset
uspto-grants-2003_04
Patent number
US06555704B1

Reaction notes

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