Methyl Acrylate → Gamma-Decalactone

HRID 599719

Reaction equation

HRID 599719 reaction equation
[CH2:1](O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]C.[C:9]([O:13][CH3:14])(=[O:12])[CH:10]=[CH2:11].C(OOC(C)(C)C)(C)(C)C>[Br-].[Zn+2].[Br-]>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH:14]1[O:13][C:9](=[O:12])[CH2:10][CH2:11]1

Participants

5

Reactant 3

HCID 7294Methyl AcrylateHCID 8033Di-tert-butyl peroxideHCID 8129Heptanol

Product 1

HCID 12813Gamma-Decalactone

Reagents, catalysts & solvents 1

HCID 10421208Zinc bromideCatalyst

Conditions

Temperature
165 °C

Procedure

To an autoclave (a volume of 1 L) was charged 349 g (3.0 mol) of n-heptanol and 0.06 g (0.27 mmol) of zinc bromide. The mixture was heated and stirred at 165° C. Into the mixture in this state was injected a mixed liquor of 57 g (0.66 mol) of methyl acrylate and 9.9 g (0.068 mol) of di-t-butylperoxide over 6 hours. The resulting mixture was stirred at the temperature for further 1 hour. Subsequently, unreacted n-heptanol was distilled off followed by vacuum distillation, yielding γ-decalactone. Gas chromatographic analysis showed that the yield of γ-decalactone was 69%. The resulting γ-decalactone was plastic-like in odor and acidulous, which indicated an inferior aroma.

Workup

  1. temperatureThe mixture was heated
  2. customover 6 hours
  3. stirringThe resulting mixture was stirred at the temperature for further 1 hour
  4. distillationSubsequently, unreacted n-heptanol was distilled off
  5. distillationfollowed by vacuum distillation

Sources & evidence

ORD record
ord-3d1c89f5dbb44175a99bc0e45cabbbda
Source dataset
uspto-grants-2011_03
Patent number
US07897802B2

Linked notes

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