Methyl Chloride → HCID 19378284, compound

HRID 2210401Notes

Reaction equation

HRID 2210401 reaction equation
[C:1]([Cl:10])([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[CH3:11]Cl.[CH3:13][C:14](=[CH2:16])[CH3:15].B(Cl)(Cl)Cl.CCC[CH2:24][CH2:25][CH3:26]>CO>[Cl:10][C:1]([C:4]1[CH:9]=[C:8]([C:14]([CH3:15])([CH3:13])[CH3:16])[CH:7]=[C:6]([C:25]([CH3:24])([CH3:26])[CH3:11])[CH:5]=1)([CH3:3])[CH3:2]

Participants

7

Reactant 5

HCID 6327Methyl ChlorideHCID 8058HexaneHCID 8255IsobutyleneHCID 25135Boron TrichlorideHCID 70281(1-Chloro-1-methylethyl)benzene

Product 1

HCID 19378284HCID 19378284, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The following procedure is conducted in a dry box under dry N2 atmosphere at -40° C. Into a 500 mL three-necked, round-bottomed flask equipped with mechanical stirrer are added 30 g (0.19 mole) cumyl chloride, 200 mL hexane, 200 mL methyl chloride, and 11.4 g (0.20 mole) isobutylene. With vigorous stirring, 50 g (0.43 mole) BCl3 is added rapidly to the mixture. After 10 minutes, 45 mL pre-chilled MeOH is added to terminate the reaction, and the reactor is removed from the dry-box. The MeCl2 is caused to evaporate as the contents of the reactor are allowed to warm to room temperature with stirring. The remaining mixture is washed twice with 200 mL of 0.5N aqueous HCl and twice with 200 mL distilled water and then dried over MgSO4. The product is isolated by evaporation of the hexane.

Workup

  1. customThe following procedure is conducted in a dry box under dry N2 atmosphere at -40° C
  2. customInto a 500 mL three-necked, round-bottomed flask equipped with mechanical stirrer
  3. additionis added
  4. customto terminate
  5. customthe reaction
  6. customthe reactor is removed from the dry-box
  7. customto evaporate as the contents of the reactor
  8. washThe remaining mixture is washed twice with 200 mL of 0.5N aqueous HCl and twice with 200 mL
  9. distillationdistilled water
  10. dry with materialdried over MgSO4
  11. customThe product is isolated by evaporation of the hexane

Sources & evidence

ORD record
ord-8a4e677da7d64c7986508184c99ac295
Source dataset
uspto-grants-1995_10
Patent number
US05458796

Reaction notes

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