Benzyl Alcohol → Benzyl mesylate

HRID 614562

Reaktionsgleichung

Reaktionsgleichung von HRID 614562
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:16][S:17](Cl)(=[O:19])=[O:18]>ClCCl>[CH3:16][S:17]([O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)(=[O:19])=[O:18]

Komponenten

5

Edukt 3

HCID 244Benzyl AlcoholHCID 8471TriethylamineHCID 31297Methanesulfonyl chloride

Produkt 1

HCID 148757Benzyl mesylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To an ice cooled solution of 54 g (0.5 mol) of benzyl alcohol and 75.75 g (104.3 ml, 0.75 mol) of triethylamine in 1800 ml of dichloromethane is added dropwise 63 g (42.57 ml, 0.55 mol) of methanesulfonyl chloride. The temperature of the reaction mixture during the addition is ca. 10°. The reaction mixture is then stirred for 1.5 hours at 10°. The reaction mixture is then diluted with dichloromethane, washed with ice water, cold 10% HCl, saturated KHCO3, saturated NaCl and dried (MgSO4). Solvent is removed in vacuo to yield the benzyl methanesulfonate as an oil.

Aufarbeitung

  1. additionThe temperature of the reaction mixture during the addition
  2. customis ca. 10°
  3. washwashed with ice water, cold 10% HCl, saturated KHCO3, saturated NaCl
  4. dry with materialdried (MgSO4)
  5. customSolvent is removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-142440ae98ad4ede98e4142a5d04f31d
Quelldatensatz
uspto-grants-1979_03
Patentnummer
US04145433

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