Ethyl formate → HCID 69828478, compound

HRID 2306153Notes

Reaction equation

HRID 2306153 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[CH2:9][C:10]#[N:11].[CH:12](OCC)=[O:13].[K].CC(C)([O-])C>C1(C)C=CC=CC=1>[OH:13][CH:12]=[C:9]([C:3]1[C:4]([CH3:8])=[CH:5][CH:6]=[CH:7][C:2]=1[CH3:1])[C:10]#[N:11]

Participants

5

Reactant 3

HCID 8025Ethyl formateHCID 40369412,6-DIMETHYLPHENYLACETONITRILEHCID 50987170Potassium tertbutoxide

Product 1

HCID 69828478HCID 69828478, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

126 g (0.87 mol) of 2,6-dimethylphenylacetonitrile are dissolved in 450 ml toluene and combined with 450 ml of ethyl formate. The mixture is cooled to a temperature of −10° C. and 144 g (1.29 mol) of potassium-tert.-butoxide are added in batches, so that the temperature does not exceed −5° C. It is left to react for a period of 30 minutes (min) at −5° C. and then for 2 hours (h) at ambient temperature. It is then extracted twice with 500 ml of water, the aqueous phase is made acidic with 100 ml of concentrated hydrochloric acid and extracted twice more with 500 ml of methylene chloride (dichloromethane). The organic phase is dried and concentrated by evaporation in vacuo. The residue is recrystallised from petroleum ether. Yield: 139 g (92% of theory).

Workup

  1. additionare added in batches, so that the temperature
  2. customdoes not exceed −5° C
  3. waitIt is left
  4. customto react for a period of 30 minutes (min) at −5° C.
  5. extractionIt is then extracted twice with 500 ml of water
  6. extractionextracted twice more with 500 ml of methylene chloride (dichloromethane)
  7. customThe organic phase is dried
  8. concentrationconcentrated by evaporation in vacuo
  9. customThe residue is recrystallised from petroleum ether

Sources & evidence

ORD record
ord-aa60dee087ba4624a391d4b71fdcf6a0
Source dataset
uspto-grants-2002_08
Patent number
US06441237B1

Reaction notes

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