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

HRID 2061281

反応式

HRID 2061281 の反応式
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

参加物

8

反応物 3

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

生成物 1

HCID 166558484-(2,3-Dihydroxypropoxy)benzaldehyde

試薬・触媒・溶媒 4

HCID 30318Osmium Tetroxide触媒HCID 962Water溶媒HCID 6386tert-Butanol溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-e2611f0ac641440cb0e3bafc8e0d7b15
出典データセット
uspto-grants-2012_10
特許番号
USRE043728E1

関連ノート

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