Dimethyl Sulfide → Neryl chloride

HRID 1458294

Reaktionsgleichung

Reaktionsgleichung von HRID 1458294
[Cl:1]N1C(=O)CCC1=O.CSC.O[CH2:13]/[CH:14]=[C:15](/[CH3:22])\[CH2:16][CH2:17][CH:18]=[C:19]([CH3:21])[CH3:20]>ClCCl>[CH2:13]([Cl:1])/[CH:14]=[C:15](\[CH2:16][CH2:17][CH:18]=[C:19]([CH3:21])[CH3:20])/[CH3:22]

Komponenten

5

Edukt 3

HCID 1068Dimethyl SulfideHCID 31398ChlorosuccinimideHCID 643820Nerol

Produkt 1

HCID 5874259Neryl chloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of N-chlorosuccinimide (10.0 g) and dimethylsulfide (6.56 ml) in dichloromethane (200 ml) was added nerol (7.71 g) while being cooled with ice. The mixture was stirred at 0° C. for 4 hours. The reaction solution was washed with brine and dried over sodium sulfate anhydride. Then, the solvent was evaporated, thereby yielding a raw product of neryl chloride. In a manner similar to Reference Example 1, this raw product was reacted with methyl 4- hydroxybenzoate (7.61 g) and then hydrolyzed to yield 7.47 g (55%) of 4- neryloxybenzoic acid.

Aufarbeitung

  1. temperaturewhile being cooled with ice
  2. washThe reaction solution was washed with brine
  3. dry with materialdried over sodium sulfate anhydride
  4. customThen, the solvent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-5ee97ca79b524419b25d3fb838c02837
Quelldatensatz
uspto-grants-1998_12
Patentnummer
US05849930

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