Methanol → 2,4,4-Trimethyl-3-oxopentanenitrile

HRID 986831Notes

Reaction equation

HRID 986831 reaction equation
[C:1]([O:7]C)(=O)[C:2]([CH3:5])([CH3:4])[CH3:3].[H-].[Na+].CO.[C:13](#[N:16])[CH2:14][CH3:15]>C1(C)C=CC=CC=1>[CH3:15][CH:14]([C:1](=[O:7])[C:2]([CH3:5])([CH3:4])[CH3:3])[C:13]#[N:16]

Participants

6

Reactant 4

HCID 887MethanolHCID 7854PropionitrileHCID 24758Sodium hydrideHCID 69027Methyl pivalate

Product 1

HCID 1224002,4,4-Trimethyl-3-oxopentanenitrile

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

234.6 grams (2 moles) of methyl pivalate and 120 grams (2 moles) of sodium hydride (80 weight % suspension in white oil) were heated to 90° C. in 1500 ml of dry toluene. There were dropped in at this temperature after addition of 1 ml of methanol 233.3 grams (2 moles) of propionitrile within 2.5 hours. After the end of the development of hydrogen the suspension was extracted with a total of 1200 ml of water and after phase separation the aqueous phase was acidified with concentrated HCl to a pH of 2. The deposited oil was separated off, the water phase extracted with chloroform, the organic extracts combined, dried and concentrated. The residue was fractionated in a water jet vacuum. 2,4,4-trimethyl-3-oxopentanenitrile came over at 87° C./11 Torr in an amount of 226.1 grams (81.2% of theory).

Workup

  1. additionThere were dropped in at this temperature
  2. extractionAfter the end of the development of hydrogen the suspension was extracted with a total of 1200 ml of water
  3. customafter phase separation the aqueous phase
  4. customThe deposited oil was separated off
  5. extractionthe water phase extracted with chloroform
  6. customdried
  7. concentrationconcentrated
  8. customcame over at 87° C./11 Torr in an amount of 226.1 grams (81.2% of theory)

Sources & evidence

ORD record
ord-644964fe1cae45b0af1dd824f177f091
Source dataset
uspto-grants-1987_12
Patent number
US04716237

Reaction notes

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