Sodium Hydroxide → 2-(4-Methoxyphenyl)-2-trifluoromethylpropionitrile

HRID 414276Notes

Reaction equation

HRID 414276 reaction equation
C[Si]([C:5]#[N:6])(C)C.Cl[C:8]([C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1)([C:10]([F:13])([F:12])[F:11])[CH3:9].[OH-].[Na+]>C(Cl)Cl.[Ti](Cl)(Cl)(Cl)Cl>[CH3:21][O:20][C:17]1[CH:16]=[CH:15][C:14]([C:8]([C:10]([F:11])([F:13])[F:12])([CH3:9])[C:5]#[N:6])=[CH:19][CH:18]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 82115Trimethylsilyl cyanideHCID 138856001-Chloro-1-(4-methoxyphenyl)-1-trifluoromethylethane

Product 1

HCID 138856012-(4-Methoxyphenyl)-2-trifluoromethylpropionitrileYield 93%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

Trimethylsilyl cyanide (65.1 ml; 423 mmol) was added at room temperature to 1-chloro-1-(4-methoxyphenyl)-1-trifluoromethylethane (77.6 g; 335.5 mmol) in methylene chloride (975 ml) followed by titanium tetrachloride (32.5 ml; 3.25 mmol). After stirring for 20 hours at room temparature, 2N sodium hydroxide was added carefully, dropwise, until the mixture was neutral and the precipitate separated over celite. The aqueous phase was extracted with ethyl acetate and the extract dried over sodium suphate. After concentrating, there was obtained 2-(4-methoxyphenyl)-2-trifluoromethylpropionitrile (71.49 g=90% of theory).

Workup

  1. additionwas added carefully
  2. customthe precipitate separated over celite
  3. extractionThe aqueous phase was extracted with ethyl acetate
  4. dry with materialthe extract dried over sodium suphate
  5. concentrationAfter concentrating

Sources & evidence

ORD record
ord-0985a8a20a6845289122f17cfb693fd6
Source dataset
uspto-grants-1988_12
Patent number
US04791123

Reaction notes

Loading…