Methylglyoxal → 2,5-Dioxo-3-hydroxy-8-nonyne

HRID 66952

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HRID 66952 반응식
[OH-:1].[Na+].S(=O)(=O)(O)O.[CH3:8][C:9]([CH:11]=[O:12])=[O:10].[C:13]1(C)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>>[O:10]=[C:9]([CH:11]([OH:12])[CH2:13][C:14](=[O:1])[CH2:15][CH2:16][C:17]#[CH:18])[CH3:8]

참가 물질

5

반응물 4

HCID 880MethylglyoxalHCID 1118Sulfuric AcidHCID 1140TolueneHCID 14798Sodium Hydroxide

생성물 1

HCID 129396472,5-Dioxo-3-hydroxy-8-nonyne수율 83.8%

반응 조건

온도
30 °C

실험 절차

To diethyl 2-(2'-propnynyl)-3-oxoglutarate (24.0 g) was added a 10% aqueous sodium hydroxide solution (sodium hydroxide 8.0 g, water 72 ml) with ice cooling, followed by stirring at 30° C. for 5 hours. The pH of the reaction solution was adjusted to 7.5 with a 10% sulfuric acid with ice cooling, and toluene (60 ml) was added thereto. While passing nitrogen stream, a 40.7% aqueous methylglyoxal solution (20 g) was added dropwise to the reaction solution at 35° C. over 2 hours. Thereafter, the reaction solution was stirred at 35° C. for 15 hours. The reaction solution was separated into two layers, and the aqueous layer was saturated with sodium chloride and extracted three times with ethyl acetate. The toluene layer and the ethyl acetate layer were combined, and the solvent was removed by evaporation to obtain 14.1 g of 2,5-dioxo-3-hydroxy-8-nonyne as a pale yellow oil. Yield 83.8%. nD23 1.4593.

후처리

  1. additionwas added
  2. stirringThereafter, the reaction solution was stirred at 35° C. for 15 hours
  3. customThe reaction solution was separated into two layers
  4. extractionextracted three times with ethyl acetate
  5. customthe solvent was removed by evaporation

출처 및 근거

ORD 기록
ord-34c75ce973774e58ac091d04d2526c7f
출처 데이터셋
uspto-grants-1982_08
특허 번호
US04343953

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