Chloroacetonitrile → HCID 54204577, compound

HRID 1680258Notes

Reaction equation

HRID 1680258 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]([OH:17])([C:13]([F:16])([F:15])[F:14])[C:9]([F:12])([F:11])[F:10])[CH:5]=[C:4]([CH3:18])[C:3]=1[OH:19].Cl[CH2:21][C:22]#[N:23].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[F:16][C:13]([F:14])([F:15])[C:8]([C:6]1[CH:5]=[C:4]([CH3:18])[C:3]([O:19][CH2:21][C:22]#[N:23])=[C:2]([CH3:1])[CH:7]=1)([OH:17])[C:9]([F:10])([F:11])[F:12]

Participants

5

Reactant 3

HCID 7856Chloroacetonitrile2×HCID 11430Potassium CarbonateHCID 706609HCID 706609, compound

Product 1

HCID 54204577HCID 54204577, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To 2,6-dimethyl-4-(hexafluoro-2-hydroxy-2-propyl)phenol (12.0 g=42 mmol) in 150 ml acetonitrile add chloroacetonitrile (3.8 g=50 mmol) and potassium carbonate (11.5 g=83 mmol). Reflux 6 hours, add more chloroacetonitrile (0.8 g=10 mmol), reflux 1/2 hour, and allow to cool. Filter, concentrate and partition between ether and water. Dry and concentrate the ether. Partition between 1:9 ether-hexane and 1.0 N NaOH. Acidify the aqueous layer with concentrated HCl and extract with ether. Dry and concentrate the combined ether extracts to leave a residue comprising 2-[4-(hexafluoro-2-hydroxy-2-propyl)-2,6-dimethylphenoxy]acetonitrile, together with some of the corresponding acetamide.

Workup

  1. temperatureReflux 6 hours
  2. temperaturereflux 1/2 hour
  3. temperatureto cool
  4. filtrationFilter
  5. concentrationconcentrate
  6. custompartition between ether and water
  7. customDry
  8. concentrationconcentrate the ether
  9. customPartition between 1:9 ether-hexane and 1.0 N NaOH
  10. extractionextract with ether
  11. customDry
  12. concentrationconcentrate the combined ether

Sources & evidence

ORD record
ord-b6c8299c7fde452ab5638bf1d8e62703
Source dataset
uspto-grants-1981_06
Patent number
US04272550

Reaction notes

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