Water → 4-(4'-Trifluoromethylphenoxy)-alpha-phenoxy-propionic acid cyanomethyl ester

HRID 902994Notes

Reaction equation

HRID 902994 reaction equation
[F:1][C:2]([F:23])([F:22])[C:3]1[CH:21]=[CH:20][C:6]([O:7][C:8]2[CH:19]=[CH:18][C:11]([O:12][CH:13]([CH3:17])[C:14](Cl)=[O:15])=[CH:10][CH:9]=2)=[CH:5][CH:4]=1.[OH:24][CH2:25][C:26]#[N:27].C(N(CC)CC)C.O>C(Cl)Cl>[C:26]([CH2:25][O:24][C:14](=[O:15])[CH:13]([O:12][C:11]1[CH:10]=[CH:9][C:8]([O:7][C:6]2[CH:20]=[CH:21][C:3]([C:2]([F:23])([F:1])[F:22])=[CH:4][CH:5]=2)=[CH:19][CH:18]=1)[CH3:17])#[N:27]

Participants

6

Reactant 4

HCID 962WaterHCID 7857HydroxyacetonitrileHCID 8471TriethylamineHCID 129060152-{4-[4-(Trifluoromethyl)phenoxy]phenoxy}propanoyl chloride

Product 1

HCID 542118074-(4'-Trifluoromethylphenoxy)-alpha-phenoxy-propionic acid cyanomethyl esterYield 72.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

17.2 g (0.05 mole) of 4-(4'-trifluoromethylphenoxy)-α-phenoxypropionyl chloride are added dropwise at 10° C. to a mixture of 3.13 g (0.055 mole) of 100% hydroxyacetonitrile (cyanomethanol) and 5.5 g (0.54 mole) of triethylamine in 50 ml of methylene chloride. The reaction mixture is then stirred for 1 hour at room temperature. Then 100 ml of water are added and the organic phase is separated, filtered over a small column of silica gel and concentrated. The residual solid is triturated with petroleum ether, collected by filtration and dried, affording 13.2 g (72.5% of theory) of 4-(4'-trifluoromethylphenoxy)-α-phenoxy-propionic acid cyanomethyl ester with a melting point of 53°-56° C.

Workup

  1. customthe organic phase is separated
  2. filtrationfiltered over a small column of silica gel
  3. concentrationconcentrated
  4. customThe residual solid is triturated with petroleum ether
  5. filtrationcollected by filtration
  6. customdried

Sources & evidence

ORD record
ord-ae3eba629c75405db67ee891671ea43d
Source dataset
uspto-grants-1980_10
Patent number
US04226614

Reaction notes

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