1,2-Dimethoxyethane → HCID 22754230, compound

HRID 1679341Notes

Reaction equation

HRID 1679341 reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([F:11])([F:10])[F:9])[N:3]=1.[CH3:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1.[OH-].[K+].C(COC)OC>O.CN(C)P(N(C)C)(N(C)C)=O>[F:9][C:8]([F:11])([F:10])[C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([O:20][C:17]2[CH:18]=[CH:19][C:14]([O:13][CH3:12])=[CH:15][CH:16]=2)[N:3]=1

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 90154-MethoxyphenolHCID 14797Potassium HydroxideHCID 6023342-Chloro-6-(trifluoromethyl)pyridine

Product 1

HCID 22754230HCID 22754230, compoundYield 94.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 12679HexamethylphosphoramideSolvent

Procedure

A mixture comprising 90.5 grams (0.5 mole) of 2-chloro-6-trifluoromethylpyridine, 65 grams (0.55 mole) of 4-methoxyphenol and 36.4 grams (0.55 mole) of 85 percent potassium hydroxide was stirred in 1 liter of a 1:1 mixture of monoglyme and hexamethylphosphoramide for 1 hour at room temperature and thereafter heated overnight at reflux. The resulting mixture was diluted with water and extracted with hexane. The hexane extract was washed with a dilute sodium hydroxide solution followed by water washing. The extract was dried and concentrated under reduced pressure to give 127 grams (94 percent of theoretical) of 2-trifluoromethyl-6-(4-methoxyphenoxy)pyridine.

Workup

  1. temperatureheated overnight
  2. temperatureat reflux
  3. extractionextracted with hexane
  4. extractionThe hexane extract
  5. washwas washed with a dilute sodium hydroxide solution
  6. customThe extract was dried
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-bece74011ca940cb8b70bc20058a5222
Source dataset
uspto-grants-1978_03
Patent number
US04080443

Reaction notes

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