Sodium Hydroxide → Methyl 4-oxodecanoate

HRID 599714

반응식

HRID 599714 반응식
[O:1]=[C:2]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH2:3][CH2:4][C:5]([O:7][CH2:8]C(C)C)=[O:6].[OH-].[Na+]>CO>[O:1]=[C:2]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH2:3][CH2:4][C:5]([O:7][CH3:8])=[O:6]

참가 물질

4

반응물 2

HCID 14798Sodium HydroxideHCID 252092612-Methylpropyl 4-oxodecanoate

생성물 1

HCID 538627Methyl 4-oxodecanoate

시약·촉매·용매 1

HCID 887Methanol용매

반응 조건

온도
25 °C

실험 절차

To the resulting isobutyl 4-oxodecanoate were added 1 L of methanol and 250 g of 25% sodium hydroxide, and the mixture was stirred at 25° C. for 1 hour, followed by distilling off methanol in vacuo. Subsequently, thereto were added 2 L of water and 1 L of toluene. The resulting mixture was stirred at room temperature for 1 hour and then allowed to stand to separate the water phase. To the water phase were added 175 g of concentrated hydrochloric acid and 1.8 L of toluene. The resulting mixture was stirred for 10 minutes and then allowed to stand to separate the organic phase. Toluene in the organic phase was distilled off in vacuo and 1 L of toluene and 47.5 mL of concentrated sulfuric acid were added. The resulting mixture was heated under reflux for 1 hour and then cooled to 25° C. Thereto was gradually added 155 g of sodium hydrogencarbonate followed by stirring for 10 minutes at 25° C. Methanol was distilled off in vacuo and then 3 L of water and 1.8 L of toluene were added. The resulting mixture was stirred for 10 minutes at room temperature and then allowed to stand to separate the organic phase. Toluene in the organic phase was distilled off, yielding methyl 4-oxodecanoate (a compound in which R17 represents an n-pentyl group, and R18 represents a methyl group in the above formula (12)). Gas chromatographic analysis showed that the yield of methyl 4-oxodecanoate relative to isobutyl 4-oxodecanoate was 95%.

후처리

  1. distillationby distilling off methanol in vacuo
  2. additionSubsequently, thereto were added 2 L of water and 1 L of toluene
  3. stirringThe resulting mixture was stirred at room temperature for 1 hour
  4. customto separate the water phase
  5. additionTo the water phase were added 175 g of concentrated hydrochloric acid and 1.8 L of toluene
  6. stirringThe resulting mixture was stirred for 10 minutes
  7. customto separate the organic phase
  8. distillationToluene in the organic phase was distilled off in vacuo and 1 L of toluene and 47.5 mL of concentrated sulfuric acid
  9. additionwere added
  10. temperatureThe resulting mixture was heated
  11. temperatureunder reflux for 1 hour
  12. temperaturecooled to 25° C
  13. stirringby stirring for 10 minutes at 25° C
  14. distillationMethanol was distilled off in vacuo
  15. addition3 L of water and 1.8 L of toluene were added
  16. stirringThe resulting mixture was stirred for 10 minutes at room temperature
  17. customto separate the organic phase
  18. distillationToluene in the organic phase was distilled off

출처 및 근거

ORD 기록
ord-0535824467e640658d22b42a72a705c0
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07897802B2

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