Dimethyl Sulfide → Neryl chloride

HRID 1458294

Reaction equation

HRID 1458294 reaction equation
[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]

Participants

5

Reactant 3

HCID 1068Dimethyl SulfideHCID 31398ChlorosuccinimideHCID 643820Nerol

Product 1

HCID 5874259Neryl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-5ee97ca79b524419b25d3fb838c02837
Source dataset
uspto-grants-1998_12
Patent number
US05849930

Linked notes

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