1-Phenyl-1-propanol → (1-Chloropropyl)benzene

HRID 1594177Notes

Reaction equation

HRID 1594177 reaction equation
[C:1]1([CH:7](O)[CH2:8][CH3:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(C(C)C)C(C)C)C.CS([Cl:24])(=O)=O>ClCCl.C(=O)(O)[O-].[Na+]>[Cl:24][CH:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH2:8][CH3:9]

Participants

6

Reactant 3

HCID 71471-Phenyl-1-propanolHCID 31297Methanesulfonyl chlorideHCID 81531Diisopropylethylamine

Product 1

HCID 524241(1-Chloropropyl)benzeneYield 54%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

Under ice cooling, to a solution of 1-phenyl-1-propanol (1.0 g, 7.34 mmol) and N-ethyldiisopropylamine (1.42 g, 11.01 mmol) in dichioromethane (10 ml) was added methanesulfonyl chloride (690 μl, 8.81 mmol), and the mixture was stirred at room temperature for 5 hours. The reaction mixture was diluted with saturated aqueous solution of sodium bicarbonate and extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate, and solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography (eluent:ethyl acetate/hexane:5/1) to give 1-chloro-1-phenylpropane (610 mg, 54%) as pale yellow liquid.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over magnesium sulfate, and solvent
  4. distillationwas distilled off under reduced pressure
  5. customThe residue was purified by silica gel chromatography (eluent:ethyl acetate/hexane:5/1)

Sources & evidence

ORD record
ord-e1a67c15ed304ecdb3842a91b3f25aa4
Source dataset
uspto-grants-2007_11
Patent number
US07300935B2

Reaction notes

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