Potassium Hydroxide → Ethyl 3-oxovalerate

HRID 1680496Notes

Reaction equation

HRID 1680496 reaction equation
COCC[O:5][C:6]1[CH:12]=[CH:11][C:9](N)=[CH:8]C=1.N([O-])=[O:14].[Na+].[C:17]([O-])(=O)[CH3:18].[Na+].[OH-:22].[K+]>Cl.O.C(O)C.C1(C)C=CC=CC=1>[CH2:17]([O:22][C:6](=[O:5])[CH2:12][C:11](=[O:14])[CH2:9][CH3:8])[CH3:18]

Participants

9

Reactant 4

HCID 14797Potassium HydroxideHCID 517045Sodium AcetateHCID 38798854-(2-Methoxyethoxy)anilineHCID 23668193Sodium Nitrite

Product 1

HCID 78656Ethyl 3-oxovalerateYield 110.2%

Reagents, catalysts & solvents 4

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolventHCID 962WaterSolvent3×HCID 1140TolueneSolvent2×

Procedure

50 g of 4-(β-methoxyethoxy)-aniline in 76.5 ml of strong hydrochloric acid and 50 ml of water are diazotized at 0° C. by the dropwise addition of a solution of 22.8 g of sodium nitrite in 70 ml of water. The reaction mixture is stirred for 1 h whereupon 32 g of sodium acetate are added. Then a solution of 47.5 g of α-methylacetylacetic acid ethyl ester in 300 ml of ethanol is prepared, to which a solution of 21.6 g of potassium hydroxide in 30 ml of water is added dropwise at 0° C. Then successively 300 g of ice and the diazonium solution are added, whereupon the mixture is stirred for another 4 h. The mixture is shaken out with toluene, whereupon the toluene is evaporated. Yield: 77.5 g of a reddish brown oil, which is transformed without any further purification.

Workup

  1. additionare added
  2. additionis added dropwise at 0° C
  3. customis evaporated
  4. customYield: 77.5 g of a reddish brown oil, which is transformed without any further purification

Sources & evidence

ORD record
ord-518c06a0b33f461190da76a0a2ea438f
Source dataset
uspto-grants-1981_06
Patent number
US04273855

Reaction notes

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