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Sulfuric Acid → Dicetyl malonate

HRID 2088325
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HRID 2088325 반응식
OS(O)(=O)=O.[C:6]([O:13][CH3:14])(=[O:12])[CH2:7][C:8]([O:10][CH3:11])=[O:9].C(O)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30].C(O[C:35](=O)[CH3:36])C.[CH3:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43]>ClCCl>[C:6]([O:13][CH2:14][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH3:16])(=[O:12])[CH2:7][C:8]([O:10][CH2:11][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:35][CH3:36])=[O:9]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 1118Sulfuric AcidHCID 2682Cetyl AlcoholHCID 7943Dimethyl malonate2회HCID 21226206Ethyl acetate hexane

생성물 1

HCID 219487Dicetyl malonate

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

H2SO4 (conc) (0.1 mL, 0.0036 mol % was slowly added to a mixture of dimethyl malonate (2 g, 0.015 mol) and hexadecanol (15 mL, 0.061 mol) and the mixture was heated at reflux until all dimethyl malonate was converted according to TLC (approximately 4 days). The product mixture was dissolved in dichloromethane (DCM), extracted with water (3 times) and dried over MgSO4. An analytically pure sample was obtained by column chromatography on silica gel using a 1:9 mixture of ethylacetate/hexane. Yield: 5.5 g (65.7%), see JP 57067510.

후처리

  1. temperaturethe mixture was heated
  2. customwas converted according to TLC (approximately 4 days)
  3. extractionextracted with water (3 times)
  4. dry with materialdried over MgSO4
  5. customAn analytically pure sample was obtained by column chromatography on silica gel using

출처 및 근거

ORD 기록
ord-a60e5b7ee8f84f738510cb7d0010cf7d
출처 데이터셋
uspto-grants-2013_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08435931B2

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