Acetic Acid → HCID 15461889, compound

HRID 2306154Notes

Reaction equation

HRID 2306154 reaction equation
[OH:1][CH:2]=[C:3]([C:6]1[C:11]([CH3:12])=[CH:10][CH:9]=[CH:8][C:7]=1[CH3:13])[C:4]#[N:5].C([BH3-])#N.[Na+].C(O)(=O)C>CO>[OH:1][CH2:2][CH:3]([C:6]1[C:11]([CH3:12])=[CH:10][CH:9]=[CH:8][C:7]=1[CH3:13])[C:4]#[N:5]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 5003444Sodium cyanoborohydrideHCID 69828478HCID 69828478, compound

Product 1

HCID 15461889HCID 15461889, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

58 g (0.33 mol) of hydroxymethylene-2,6-dimethylphenylacetonitrile are dissolved in 250 ml methanol and combined with 37 g (0.59 mol) of sodium cyanoborohydride. After 2 h, 250 ml of acetic acid are added dropwise, during which time the mixture heats up to 50° C. After the exothermic reaction has died down, the mixture is refluxed for a further 3 h. It is left to cool and the mixture is evaporated down in vacuo. The residue is mixed with 500 g of ice, neutralised with ammonia and extracted twice with 500 ml of ethyl acetate. The combined organic extracts are washed with 100 ml of water. After drying, the solvent is eliminated in vacuo. The residue is further processed from the crude state. 54.1 g (92% of theory) of the title compounds are obtained in the form of an oil.

Workup

  1. customheats up to 50° C
  2. customAfter the exothermic reaction
  3. temperaturethe mixture is refluxed for a further 3 h
  4. waitIt is left
  5. temperatureto cool
  6. customthe mixture is evaporated down in vacuo
  7. additionThe residue is mixed with 500 g of ice
  8. extractionextracted twice with 500 ml of ethyl acetate
  9. washThe combined organic extracts are washed with 100 ml of water
  10. customAfter drying

Sources & evidence

ORD record
ord-4121865a1b524acc8f6a9a5b838f1958
Source dataset
uspto-grants-2002_08
Patent number
US06441237B1

Reaction notes

Loading…