Water → 2-Chloro-2,4,4-trimethylpentane

HRID 64943

Reaction equation

HRID 64943 reaction equation
[CH3:1][C:2]([CH2:4][C:5]([CH3:8])([CH3:7])[CH3:6])=[CH2:3].S(Cl)([Cl:11])=O.O>C(Cl)Cl>[Cl:11][C:2]([CH3:1])([CH2:4][C:5]([CH3:8])([CH3:7])[CH3:6])[CH3:3]

Participants

5

Reactant 3

HCID 962WaterHCID 78682,4,4-Trimethyl-1-penteneHCID 24386Thionyl Chloride

Product 1

HCID 5219502-Chloro-2,4,4-trimethylpentaneYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-30 °C

Procedure

15 ml of 2,4,4-trimethyl-pentene-1 are dissolved in 150 ml of CH2Cl2, cooled to -30° C. and mixed dropwise with a mixture of 10.3 ml of thionyl chloride and 5.4 ml of H2O. The mixture is then heated to 0° C. and washed after 2.5 hours with cold 1% aqueous K2CO3 solution, then with ice-cold water. The product is dried over MgSO4 and distilled off. Yield 85%; nD20 =1.4308; Bpt.10 mm 38° C.

Workup

  1. temperatureThe mixture is then heated to 0° C.
  2. washwashed after 2.5 hours with cold 1% aqueous K2CO3 solution
  3. dry with materialThe product is dried over MgSO4
  4. distillationdistilled off
  5. custom10 mm 38° C.

Sources & evidence

ORD record
ord-430db93bb1604512ad66e62ccbabb9cf
Source dataset
uspto-grants-1986_09
Patent number
US04611037

Linked notes

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