Chloroacetonitrile → HCID 20093009, compound

HRID 248400Notes

Reaction equation

HRID 248400 reaction equation
[OH:1][C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][CH:7]=1)=[O:5].Cl[CH2:18][C:19]#[N:20].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[C:19]([CH2:18][O:1][C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][CH:7]=1)=[O:5])#[N:20]

Participants

5

Reactant 3

HCID 7856ChloroacetonitrileHCID 11430Potassium CarbonateHCID 29594Benzophenone, 2-hydroxy-4'-methyl-

Product 1

HCID 20093009HCID 20093009, compoundYield 98.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-hydroxy-4'-methylbenzophenone (18.3 g), chloroacetonitrile (7.87 g) and potassium carbonate (14.2 g) in N,N'-dimethylformamide (183 ml) was stirred at ambient temperature for 5 hours and then poured into ice water. The separated oil was extracted with dichloromethane (×2). The organic layer were washed with water (×3), dried and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluted with dichloromethane to give 2-cyanomethoxy-4'-methylbenzophenone (21.3 g) as a yellow oil.

Workup

  1. extractionThe separated oil was extracted with dichloromethane (×2)
  2. washThe organic layer were washed with water (×3)
  3. customdried
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash column chromatography on silica gel
  6. washeluted with dichloromethane

Sources & evidence

ORD record
ord-5af1c23c0deb414394ae0251373be5e0
Source dataset
uspto-grants-1993_05
Patent number
US05210092

Reaction notes

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