Sodium Chloride → 2-Chloro-1-(methoxymethoxy)-3(trifluoromethyl)benzene

HRID 629354Notes

Reaction equation

HRID 629354 reaction equation
[H-].[Na+].[Cl:3][C:4]1[C:9]([OH:10])=[CH:8][CH:7]=[CH:6][C:5]=1[C:11]([F:14])([F:13])[F:12].[CH3:15][O:16][CH2:17]Cl.[Cl-].[Na+]>C1COCC1>[Cl:3][C:4]1[C:5]([C:11]([F:12])([F:13])[F:14])=[CH:6][CH:7]=[CH:8][C:9]=1[O:10][CH2:15][O:16][CH3:17]

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 27366012-Chloro-3-(trifluoromethyl)phenol

Product 1

HCID 1184684062-Chloro-1-(methoxymethoxy)-3(trifluoromethyl)benzeneYield 110.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
12 °C

Procedure

To a suspension of sodium hydride (3.78 g) in THF (150 mL) were added dropwise 2-chloro-3-hydroxybenzotrifluoride (12.4 g) and chloromethyl methyl ether (6.10 g) under ice-cooling, and the mixture was stirred at 12° C. for 16 hr. The reaction mixture was poured into saturated aqueous sodium chloride solution, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to give the title compound (16.8 g) as a crude product.

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-e1c4c1210c094fbba5cc5c99954a0f1b
Source dataset
uspto-grants-2016_04
Patent number
US09315458B2

Reaction notes

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