Acetone → 4-(2,3-Dihydroxypropoxy)benzaldehyde

HRID 1466198

반응식

HRID 1466198 반응식
C([O:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[O:10])=[CH:7][CH:6]=1)C=C.C[N+]1([O-])CC[O:17]CC1.[CH3:21][C:22]([CH3:24])=[O:23]>O.C(O)(C)(C)C.CC(=O)OCC.O=[Os](=O)(=O)=O>[OH:23][CH:22]([CH2:24][OH:17])[CH2:21][O:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[O:10])=[CH:7][CH:6]=1

참가 물질

8

반응물 3

HCID 180AcetoneHCID 82029Methyl morpholine oxideHCID 959424-(Allyloxy)benzaldehyde

생성물 1

HCID 166558484-(2,3-Dihydroxypropoxy)benzaldehyde

시약·촉매·용매 4

HCID 30318Osmium Tetroxide촉매HCID 962Water용매HCID 6386tert-Butanol용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 4-allyloxybenzaldehyde (1.0 g, 6.17 mmol) in acetone (40 mL) and water (5 mL) is added a 2.5% solution of OsO4 in tert. butanol (1.25 mL) followed by N-methyl morpholine-N-oxide (867 mg, 7.4 mmol). The pale yellow solution is stirred at rt for 6 h, diluted with EA (250 mL) and washed with 10% aq. citric acid solution (100 mL) and water (2×100 mL). The washings are extracted with EA (150 mL). The combined organic extracts are concentrated and purified by column chromatography on silica gel to give the title compound (731 mg) as a turbid oil. The title compound reversibly polymerizes upon standing. LC-MS: tR=0.58 min, [M+1+CH3CN]+=238.

후처리

  1. washwashed with 10% aq. citric acid solution (100 mL) and water (2×100 mL)
  2. extractionThe washings are extracted with EA (150 mL)
  3. concentrationThe combined organic extracts are concentrated
  4. custompurified by column chromatography on silica gel

출처 및 근거

ORD 기록
ord-322d82a83a5e44dbb40f864e04198670
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09000018B2

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