Hydrochloric Acid → 3-(Trifluoromethyl)benzenepropanal

HRID 1253374ノート

反応式

HRID 1253374 の反応式
C[O:2][C:3](=O)[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]([F:15])([F:14])[F:13])[CH:7]=1.[H-].C([Al+]C(C)C)(C)C.[Cl-].[NH4+].Cl>ClCCl.CCCCCC.O>[F:13][C:12]([F:14])([F:15])[C:8]1[CH:7]=[C:6]([CH2:5][CH2:4][CH:3]=[O:2])[CH:11]=[CH:10][CH:9]=1

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 21896610Diisopropylaluminium hydrideHCID 53230361Methyl 3-[3-(trifluoromethyl)phenyl]propanoate

生成物 1

HCID 112986123-(Trifluoromethyl)benzenepropanal収率 101.5%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6344Dichloromethane溶媒HCID 8058Hexane溶媒

実験手順

2.40 g of 3-(3-trifluoromethylphenyl)-propionic acid methyl ester synthesized in Step 1 was dissolved in 20 ml of dry dichloromethane. 13 ml of diisopropyl aluminum hydride solution (0.91 M) in hexane was dropped over 5 minutes at −78° C. under an argon atmosphere, and the mixture was stirred at the same temperature for 40 minutes. 50 ml of a saturated ammonium chloride aqueous solution was dropped, and then the mixture was stirred and the temperature was raised to room temperature. 20 ml of water and 5 ml of concentrated hydrochloric acid were added, and the resultant was separated into an aqueous layer and an organic layer. The aqueous layer was extracted with dichloromethane, and the extract was combined with the separated organic layer, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure to afford 2.12 g of the captioned compound as an oil.

後処理

  1. stirringthe mixture was stirred
  2. customthe resultant was separated into an aqueous layer
  3. extractionThe aqueous layer was extracted with dichloromethane
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-64c890373e31474e8e3db64fe1117611
出典データセット
uspto-grants-2013_06
特許番号
US08454978B2

反応ノート

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