Methyl acetoacetate → Dodecyl 3-oxobutanoate

HRID 1706845Notes

Reaction equation

HRID 1706845 reaction equation
[C:1]([O:7][CH3:8])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[CH2:9](O)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]C>CO>[C:1]([O:7][CH2:8][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH3:9])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4]

Participants

4

Reactant 2

HCID 7757Methyl acetoacetateHCID 81931-Dodecanol

Product 1

HCID 104190Dodecyl 3-oxobutanoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
165 °C

Procedure

Introduced into a reactor equipped with a stirrer mechanism, a Vigreux column with a column head and a reflux condenser are 464 g (4 moles) of methyl acetoacetate and 186 g of dodecyl alcohol. The temperature of the reaction medium is progressively raised to 165° C. and the methanol having formed is distilled until the reaction is terminated, that is to say, for about 8 hours. The methyl acetoacetate excess is eliminated under a reduced pressure of 8 mm Hg and the crude dodecyl acetoacetate is recovered, and this will be used as such for the preparation of the corresponding dihydropyridine derivative (Example 3).

Workup

  1. additionIntroduced into a reactor
  2. customequipped with a stirrer mechanism
  3. distillationis distilled until the reaction
  4. customis terminated
  5. customthe crude dodecyl acetoacetate is recovered
  6. customsuch for the preparation of the corresponding dihydropyridine derivative (Example 3)

Sources & evidence

ORD record
ord-91e3d53bae9d44b983700b368c80f3d0
Source dataset
uspto-grants-1980_06
Patent number
US04209439

Reaction notes

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