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Benzene → 2-(2-Methylpropanoyloxy)ethyl 2-methylpropanoate

HRID 2254354
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HRID 2254354 반응식
C(O)[CH2:2][CH2:3][OH:4].C1C=CC=CC=1.[C:12]([OH:17])(=[O:16])[CH:13]([CH3:15])[CH3:14].[OH2:18].[C:19]1([CH3:29])[CH:24]=CC(S(O)(=O)=O)=C[CH:20]=1>O>[CH3:14][CH:13]([CH3:15])[C:12]([O:17][CH2:2][CH2:3][O:4][C:24](=[O:18])[CH:19]([CH3:20])[CH3:29])=[O:16]
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참가 물질

6

반응물 4

HCID 241BenzeneHCID 6590Isobutyric AcidHCID 104421,3-PropanediolHCID 521998p-Toluenesulfonic acid monohydrate

생성물 1

HCID 2442882-(2-Methylpropanoyloxy)ethyl 2-methylpropanoate수율 850.4%

시약·촉매·용매 1

HCID 962Water용매

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온도
10 °C

실험 절차

A mixture of 28.0 ml (31.0 g, 0.5 mole) of ethylene glycol (VIII), 200 ml of benzene, 111.6 ml (105.8 g, 1.2 mole) of isobutyric acid and 9.5 g (0.05 mole) of p-toluenesulfonic acid monohydrate is stirred under reflux for 2.5 hours, while the water being formed is continuously separated by using a Dean-Stark apparatus. Then the mixture is cooled to about 10° C., extracted three times with 100 ml of ice-cold 1N aqueous sodium hydroxide solution, washed with water until neutral, dried over sodium sulfate and the solvent is distilled off under reduced pressure. The crude product obtained in almost quantitative yield is subjected to fractional distillation under reduced pressure. Thus 86.0 g of the desired compound are obtained in the form of a colourless oil. Yield: 85.0 %. B.p.: 74°-76° C./107 Pa. According to gas-chromatography the product is homogeneous and contains 0.3% by weight of water (determined according to Karl Fisher's method). The product thus obtained can be used directly in the next reaction step.

후처리

  1. customformed
  2. customis continuously separated
  3. extractionextracted three times with 100 ml of ice-cold 1N aqueous sodium hydroxide solution
  4. washwashed with water until neutral,
  5. dry with materialdried over sodium sulfate
  6. distillationthe solvent is distilled off under reduced pressure
  7. customThe crude product obtained in almost quantitative yield
  8. distillationis subjected to fractional distillation under reduced pressure

출처 및 근거

ORD 기록
ord-4f248dfbc1ae4fa09cf3754b82157ab5
출처 데이터셋
uspto-grants-1993_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05235097

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