1,2-Dimethoxyethane → HCID 11459000, compound

HRID 1679346Notes

Reaction equation

HRID 1679346 reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[N:3]=1.[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1.[OH-].[K+].C(COC)OC>O.CN(C)P(N(C)C)(N(C)C)=O>[Cl:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([O:17][C:14]2[CH:15]=[CH:16][C:11]([O:10][CH3:9])=[CH:12][CH:13]=2)[N:3]=1

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 90154-MethoxyphenolHCID 14797Potassium HydroxideHCID 169892,6-Dichloropyridine

Product 1

HCID 11459000HCID 11459000, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 12679HexamethylphosphoramideSolvent

Procedure

A solution comprising 14.8 grams (0.1 mole) of 2,6-dichloropyridine, 12.4 grams (0.1 mole) of 4-methoxyphenol and 8.4 grams (0.15 mole) of flake potassium hydroxide in 100 milliliters of a 1:1 mixture of monoglyme and hexamethylphosphoramide was stirred for 24 hours at room temperature. The resulting mixture was diluted with water and thoroughly extracted with hexane. The extract was washed with water, dried and concentrated under reduced pressure. The residue was recrystallized from pentane giving 14.5 grams (64 percent of theoretical) of 2-chloro-6-(4-methoxyphenoxy)pyridine which melted at 63°-65° C.

Workup

  1. extractionthoroughly extracted with hexane
  2. washThe extract was washed with water
  3. customdried
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was recrystallized from pentane giving 14.5 grams (64 percent of theoretical) of 2-chloro-6-(4-methoxyphenoxy)pyridine which melted at 63°-65° C.

Sources & evidence

ORD record
ord-e0b6e84c809e4ed39108b5a216ac58c0
Source dataset
uspto-grants-1978_03
Patent number
US04080443

Reaction notes

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