Hydrochloric Acid → 2,6-Dichloro-3-hydroxy-benzaldehyde

HRID 253433ノート

反応式

HRID 253433 の反応式
C([Si]([O:8][C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=1[Cl:16])(C)C)(C)(C)C.C([Li])CCC.CN(C)[CH:24]=[O:25].Cl>O1CCCC1.O>[Cl:16][C:10]1[C:9]([OH:8])=[CH:14][CH:13]=[C:12]([Cl:15])[C:11]=1[CH:24]=[O:25]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 59803885Tert-butyl(2,4-dichlorophenoxy)dimethylsilaneHCID 178418339Butyllithium

生成物 1

HCID 104425302,6-Dichloro-3-hydroxy-benzaldehyde

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To tert-butyl-(2,4-dichloro-phenoxy)-dimethyl-silane (113, 4.00 g, 0.0144 mol) in tetrahydrofuran (50.0 mL), under an atmosphere of nitrogen at −78° C., n-butyllithium (2.50 M in hexane, 6.06 mL) was added slowly. After 30 minutes, N,N-dimethylformamide (1.34 mL, 0.0173 mol) was added to the reaction. After 1 hour, the reaction was allowed to warm to room temperature. 1N HCl (40 mL) was added to the reaction. The reaction was poured into water and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated and purified by silica gel column chromatography eluting with 20% ethyl acetate in hexane to give a yellow solid (114, 2.0 g, 72.6%).

後処理

  1. waitAfter 1 hour
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated
  6. custompurified by silica gel column chromatography
  7. washeluting with 20% ethyl acetate in hexane
  8. customto give a yellow solid (114, 2.0 g, 72.6%)

出典と根拠

ORDレコード
ord-13535687cc4c475da14dfd123f61eafb
出典データセット
uspto-grants-2011_01
特許番号
US07872018B2

反応ノート

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