Dichloromethane → HCID 15107357, compound

HRID 2108233Notes

Reaction equation

HRID 2108233 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:15]=[CH:14][C:13]2[C:8](=C[C:10]([O:18][CH3:19])=[C:11]([O:16][CH3:17])[CH:12]=2)[CH:7]=1.S(Cl)([Cl:23])(=O)=O.[CH2:25]([Cl:27])Cl>>[Cl:23][C:12]1[C:13]2[C:8](=[CH:7][C:6]([CH2:5][CH2:4][CH2:3][CH2:2][Cl:1])=[CH:15][CH:14]=2)[C:25]([Cl:27])=[C:10]([O:18][CH3:19])[C:11]=1[O:16][CH3:17]

Participants

4

Reactant 3

HCID 6344Dichloromethane2×HCID 24648Sulfuryl chlorideHCID 15107353HCID 15107353, compound

Product 1

HCID 15107357HCID 15107357, compoundYield 79%

Conditions

Temperature
24 °C

Procedure

To a stirred solution of 3.0 g (0.011 mole) of 2-(4-chloro-butyl)-6,7-dimethoxynaphthalene in 25 mL of methylene chloride cooled in an ice bath was added 1.8 mL (0.023 mole) of sulfuryl chloride in 10 mL of methylene chloride over 15 minutes. The reaction mixture was stirred at 3° C. for 30 minutes, at 24° C. for 6 hours and then was washed with sodium bicarbonate solution, dried and concentrated under reduced pressure. Purification by HPLC using 2.5% ethyl acetate-hexane gave 3.32 g (79% yield) of 1,4-dichloro-6-(4-Chlorobutyl)-2,3-dimethoxynaphthalene as an oil.

Workup

  1. washwas washed with sodium bicarbonate solution
  2. customdried
  3. concentrationconcentrated under reduced pressure
  4. customPurification by HPLC

Sources & evidence

ORD record
ord-278527f7e3ce47ad823782c609409467
Source dataset
uspto-grants-1990_06
Patent number
US04937371

Reaction notes

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