Hydrochloric Acid → Methyl (4-cyanophenyl)acetate

HRID 1531732

Reaction equation

HRID 1531732 reaction equation
Br[CH2:2][C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][CH:4]=1.[C:11](=[O:14])([O-])[O-:12].[K+].[K+].[C:17]1(C)C=C(C)C=C(C)C=1.[C]=O.Cl>[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[Fe].O.CO>[C:7]([C:6]1[CH:9]=[CH:10][C:3]([CH2:2][C:11]([O:12][CH3:17])=[O:14])=[CH:4][CH:5]=1)#[N:8]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 7947MesityleneHCID 11430Potassium CarbonateHCID 869964-(Bromomethyl)benzonitrileHCID 178418416HCID 178418416, compound

Product 1

HCID 1512619Methyl (4-cyanophenyl)acetate

Reagents, catalysts & solvents 3

HCID 518773Pentacarbonyliron(0)CatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

30.0 g (0.15 mol) of 4-bromomethyl-benzonitrile, 2.0 ml (0.12 mol) of iron pentacarbonyl, 29.0 g potassium carbonate, 10.0 ml mesitylene and 250 ml absolute methanol are placed in a pressure vessel and about 3.5 l carbon monoxide gas is introduced. The reaction mixture is shaken for 16 hours at ambient temperature, mixed with water, neutralised with hydrochloric acid and extracted with ethyl acetate. The combined organic extracts are washed with sodium hydrogen carbonate solution, dried and evaporated down. The residue is chromatographed on silica gel and eluted with petroleum ether/ethyl acetate (9:1, 8:2 and 7:3). The desired fractions are combined and evaporated down.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic extracts are washed with sodium hydrogen carbonate solution
  3. customdried
  4. customevaporated down
  5. customThe residue is chromatographed on silica gel
  6. washeluted with petroleum ether/ethyl acetate (9:1, 8:2 and 7:3)
  7. customevaporated down

Sources & evidence

ORD record
ord-302c30427a344b1c9cdb645005d46293
Source dataset
uspto-grants-2001_03
Patent number
US06200976B1

Linked notes

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