Benzyl Alcohol → Benzyl mesylate

HRID 236071

Reaktionsgleichung

Reaktionsgleichung von HRID 236071
[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].C(Cl)Cl>O>[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

6

Edukt 4

HCID 244Benzyl AlcoholHCID 6344DichloromethaneHCID 8471TriethylamineHCID 31297Methanesulfonyl chloride

Produkt 1

HCID 148757Benzyl mesylateAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
-5 °C

Versuchsvorschrift

Under nitrogen methylene chloride (1.4 liter), benzyl alcohol (129.6 g., 1.2 moles) and triethylamine (182 g., 1.8 moles) were combined, stirred and cooled to -5° C. in an ice-water-acetone bath. A solution of methanesulfonyl chloride (150 g., 1.31 moles) in 100 ml. of methylene chloride was added over 49 minutes, maintaining the temperature between -5° and 2° C. After stirring for 10 minutes at 0°-2° C., the reaction was diluted with 500 ml. of water, precooled to 5° C. The organic layer was separated, washed 2×500 ml. of cold water, dried over MgSO4, filtered and evaporated in vacuo to yield title product as a light yellow oil [190 g.; 85%; 1H-NMR (CDCl3) delta (ppm): 2.9 (s, 3H), 5.2 (s, 2H), 7.4 (m, 5H); Rf 0.75 (CH2Cl 2)]. This product was refrigerated until used in the next step.

Aufarbeitung

  1. temperaturemaintaining the temperature between -5° and 2° C
  2. stirringAfter stirring for 10 minutes at 0°-2° C.
  3. additionthe reaction was diluted with 500 ml
  4. customprecooled to 5° C
  5. customThe organic layer was separated
  6. washwashed 2×500 ml
  7. dry with materialof cold water, dried over MgSO4
  8. filtrationfiltered
  9. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-86b84415372a4a6ea5cd775d19e3fb67
Quelldatensatz
uspto-grants-1987_02
Patentnummer
US04642373

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