Water → 4-(2,3-Dihydroxypropoxy)-3-chlorobenzaldehyde

HRID 38719

반응식

HRID 38719 반응식
[CH2:1]([O:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[O:10])=[CH:7][C:6]=1[Cl:13])[CH:2]=[CH2:3].[OH2:14].C[N+]1([O-])CC[O:19]CC1>CC(C)=O.CC(=O)OCC.O=[Os](=O)(=O)=O.C(O)(C)(C)C>[OH:14][CH:2]([CH2:3][OH:19])[CH2:1][O:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[O:10])=[CH:7][C:6]=1[Cl:13]

참가 물질

8

반응물 3

HCID 962WaterHCID 82029Methyl morpholine oxideHCID 47700363-Chloro-4-(prop-2-en-1-yloxy)benzaldehyde

생성물 1

HCID 798396484-(2,3-Dihydroxypropoxy)-3-chlorobenzaldehyde

시약·촉매·용매 4

HCID 6386tert-Butanol촉매HCID 30318Osmium Tetroxide촉매HCID 180Acetone용매HCID 8857Ethyl Acetate용매

실험 절차

The above 4-allyloxy-3-chloro-benzaldehyde (5.37 g, 27.3 mmol) is dissolved in acetone (100 mL) and water (10 mL) and treated with a 2.5% solution of OsO4 in tert.-butanol (1.71 mL, 0.137 mmol OsO4). N-methyl morpholine-N-oxide (3.87 g, 32.8 mmol) is added and the reaction mixture is stirred at rt for 20 h before it is diluted with EA (300 mL) and washed with 10% aq. citric acid solution (200 mL) and water (2×150 mL). The washings are extracted with EA (300 mL) and the combined organic extracts are dried over MgSO4, filtered and concentrated to furnish the title compound (6.02 g) as beige foam which was used in the following steps without further purification. LC: tR=0.67 min.

후처리

  1. washwashed with 10% aq. citric acid solution (200 mL) and water (2×150 mL)
  2. extractionThe washings are extracted with EA (300 mL)
  3. dry with materialthe combined organic extracts are dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-a50a026ccdeb406389225a2375678e72
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08524752B2

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