Triethylamine → Benzene, 1-butyl-4-(chloromethyl)-

HRID 1667647Notes

Reaction equation

HRID 1667647 reaction equation
CS([Cl:5])(=O)=O.[CH2:6]([C:10]1[CH:17]=[CH:16][C:13]([CH2:14]O)=[CH:12][CH:11]=1)[CH2:7][CH2:8][CH3:9].C(N(CC)CC)C>ClCCl>[CH2:6]([C:10]1[CH:17]=[CH:16][C:13]([CH2:14][Cl:5])=[CH:12][CH:11]=1)[CH2:7][CH2:8][CH3:9]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 5782884-Butylbenzyl alcohol

Product 1

HCID 182273Benzene, 1-butyl-4-(chloromethyl)-Yield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methanesulfonyl chloride (3.069 g, 26.791 mmol) was added to a solution of 4-butylbenzyl alcohol (4.000 g, 24.355 mmol) in dichloromethane (120 mL) at 0° C. under argon atmosphere. Then triethylamine (2.711 g, 26.791 mmol) was added dropwise at a slow speed to this mixture at 0° C., and the mixture was stirred overnight at room temperature. The solvent was evaporated under reduced pressure and the residue was diluted with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The residue obtained by evaporation of the solvent under reduced pressure was purified by column chromatography on silica gel (n-hexane) to give the title compound (3.64 g, 82%) as a colorless oil.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. additionthe residue was diluted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe residue obtained by evaporation of the solvent under reduced pressure
  6. customwas purified by column chromatography on silica gel (n-hexane)

Sources & evidence

ORD record
ord-f1b2c4c12dcf4b288355cd44b2a1114c
Source dataset
uspto-grants-2011_10
Patent number
US08044236B2

Reaction notes

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