Methyl acetoacetate → HCID 131709912, compound

HRID 1580328Notes

Reaction equation

HRID 1580328 reaction equation
[CH3:1][O-].[Na+].[C:4](OC)(=O)[CH2:5][C:6](C)=[O:7].[CH3:12][O:13][CH:14]([O:20][CH3:21])[C:15](C)=[CH:16][CH2:17]Cl.[OH-].[Na+]>CO>[CH3:21][O:20][C:14]([O:13][CH3:12])([CH3:1])[CH2:15][CH2:16][CH:17]=[C:5]([CH3:4])[CH:6]=[O:7]

Participants

6

Reactant 4

HCID 7757Methyl acetoacetateHCID 14798Sodium HydroxideHCID 10942334Sodium MethoxideHCID 538546664-Chloro-1,1-dimethoxy-2-methylbut-2-ene

Product 1

HCID 131709912HCID 131709912, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

180 g (1 mole) of 30% solution of sodium methylate in methanol is added over 15 minutes at 150° to 20°C to 116 g (1 mole) of methyl acetoacetate. The whole is stirred for another hour at 20° to 30° C and then 156 g (0.95 mole) of 2-methyl-4-chloro-2-buten-1-al dimethylacetal is added to the solution at 20°C over 30 minutes. The reaction mixture obtained is stirred for 15 hours at room temperature, then 400 g of 10% caustic soda solution is added and stirring is continued for another 2 hours at 60°C. The salt-like constituents are separated by filtration and the organic products are isolated by extraction with ether. Before the ethereal solution is distilled it is washed with saturated common salt solution. The ether is then distilled off and the residue is fractionated. The boiling point is 72° to 83° C at 0.9 to 1.5 mm and the refractive index nD25 = 1.4474.

Workup

  1. customThe reaction mixture obtained
  2. stirringis stirred for 15 hours at room temperature
  3. stirringstirring
  4. customThe salt-like constituents are separated by filtration
  5. customthe organic products are isolated by extraction with ether
  6. distillationBefore the ethereal solution is distilled it
  7. washis washed with saturated common salt solution
  8. distillationThe ether is then distilled off

Sources & evidence

ORD record
ord-db7feabe4b784238ab7cbf91687a7564
Source dataset
uspto-grants-1976_01
Patent number
US03932520

Reaction notes

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