p-Toluenesulfonic acid monohydrate → 4-(3,3-Dimethyl-butyryl)-benzaldehyde

HRID 911702ノート

反応式

HRID 911702 の反応式
C([O:3][CH:4](OCC)[C:5]1[CH:10]=[CH:9][C:8]([C:11](=[O:17])[CH2:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:7][CH:6]=1)C.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CC(C)=O>[CH3:14][C:13]([CH3:16])([CH3:15])[CH2:12][C:11]([C:8]1[CH:7]=[CH:6][C:5]([CH:4]=[O:3])=[CH:10][CH:9]=1)=[O:17]

参加物

4

反応物 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 576563621-[4-(Diethoxymethyl)-phenyl]-3,3-dimethylbutan-1-one

生成物 1

HCID 576561564-(3,3-Dimethyl-butyryl)-benzaldehyde収率 65.1%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

Dissolve 1-[4-(diethoxymethyl)-phenyl]-3,3-dimethylbutan-1-one (3.49 g, 12.55 mmol) in acetone (50 mL). Add p-toluenesulfonic acid monohydrate (238 mg, 1.256 mmol). Heat the mixture under reflux for 3 h. Concentrate in vacuo and partition the residue between water and EtOAc. Extract the aqueous phase three times with EtOAc. Dry the combined organic extracts over Na2SO4, filter and concentrate in vacuo. Purify the crude mixture by chromatography on silica gel eluting with hexane/EtOAc (9:1) to give the desired intermediate as a colorless oil (1.67 g, 65%).

後処理

  1. temperatureHeat the mixture
  2. temperatureunder reflux for 3 h
  3. concentrationConcentrate in vacuo
  4. custompartition the residue between water and EtOAc
  5. extractionExtract the aqueous phase three times with EtOAc
  6. dry with materialDry the combined organic extracts over Na2SO4
  7. filtrationfilter
  8. concentrationconcentrate in vacuo
  9. customPurify the crude mixture by chromatography on silica gel eluting with hexane/EtOAc (9:1)

出典と根拠

ORDレコード
ord-4020fa0628e84750b7d91e2e967badb4
出典データセット
uspto-grants-2011_09
特許番号
US08022062B2

反応ノート

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