Triethylamine → 3-(4-Cyanophenyl)propyl methanesulfonate

HRID 485278Notes

Reaction equation

HRID 485278 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[CH:7][CH:6]=1.C(N(CC)CC)C.[CH3:20][S:21](Cl)(=[O:23])=[O:22]>C(Cl)Cl>[S:21]([O:1][CH2:2][CH2:3][CH2:4][C:5]1[CH:6]=[CH:7][C:8]([C:9]#[N:10])=[CH:11][CH:12]=1)([CH3:20])(=[O:23])=[O:22]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 110841784-(3-Hydroxypropyl)benzonitrile

Product 1

HCID 219936463-(4-Cyanophenyl)propyl methanesulfonateYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 16.1 g (0.1 mol) quantity of 4-(3hydroxypropyl)benzonitrile was admixed with 27.8 ml (0.2 mol) of triethylamine and 300 ml of methylene chloride. To the mixture was added 15.5 ml (0.2 mol) of methanesulfonyl chloride at 0° C. The reaction mixture was stirred at room temperature for 12 hours and then concentrated. The concentrate was diluted with 500 ml of benzene, and washed with saturated aqueous solution of sodium chloride. The washed dilution was dried over Na2SO4 and concentrated, giving 24.0 g (yield 100%) of crude 4-(3-mesyloxypropyl)benzonitrile in the form of an oil.

Workup

  1. concentrationconcentrated
  2. additionThe concentrate was diluted with 500 ml of benzene
  3. washwashed with saturated aqueous solution of sodium chloride
  4. dry with materialThe washed dilution was dried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c352a4f37f894099960436b4cd5e8b5f
Source dataset
uspto-grants-1985_08
Patent number
US04536391

Reaction notes

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