Dichloromethane → 1-(4-Nitrophenyl)ethyl methanesulfonate

HRID 1723120

Reaktionsgleichung

Reaktionsgleichung von HRID 1723120
[CH3:1][CH:2]([C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][CH:5]=1)[OH:3].C(N(CC)CC)C.ClCCl.[CH3:23][S:24](Cl)(=[O:26])=[O:25]>O>[CH3:23][S:24]([O:3][CH:2]([C:4]1[CH:5]=[CH:6][C:7]([N+:10]([O-:12])=[O:11])=[CH:8][CH:9]=1)[CH3:1])(=[O:26])=[O:25]

Komponenten

6

Edukt 4

HCID 6344Dichloromethane2×HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 5923761-(4-Nitrophenyl)ethan-1-ol

Produkt 1

HCID 112187991-(4-Nitrophenyl)ethyl methanesulfonateAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

(a-1) To a stirred solution of 50.2 parts of α-methyl-4-nitrobenzenemethanol and 48.6 parts of N,N-diethylethanamine in 390 parts of dry dichloromethane was added dropwise a solution of 37.8 parts of methanesulfonyl chloride in 65 parts of dry dichloromethane at -5~0° C. The whole was stirred for 1 hour at 0° C. 75 Parts of cold water were added and the dichloromethane layer was decanted, dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using trichloromethane as eluent. The pure fractions were collected and the eluent was evaporated. The solid residue was shaked with 2,2'-oxybispropane. The product was filtered off and dried, yielding 67.1 parts (91%) of [1-(4-nitrophenyl)ethyl] methanesulfonate; mp. 70° C. (int. 112).

Aufarbeitung

  1. customthe dichloromethane layer was decanted
  2. customdried
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was purified by column chromatography over silica gel
  6. customThe pure fractions were collected
  7. customthe eluent was evaporated
  8. filtrationThe product was filtered off
  9. customdried

Quellen und Nachweise

ORD-Eintrag
ord-2075c749647943ad8da232aedf83b613
Quelldatensatz
uspto-grants-1989_08
Patentnummer
US04859684

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