Sulfuric Acid → 3-(3,5-Difluorophenyl)propionic acid

HRID 13690

反応式

HRID 13690 の反応式
[F:1][C:2]1[CH:3]=[C:4]([CH:10]=[C:11]([F:13])[CH:12]=1)[CH:5]=[CH:6][C:7]([OH:9])=[O:8].S(=O)(=O)(O)O>[Pd].O1CCCC1>[F:1][C:2]1[CH:3]=[C:4]([CH2:5][CH2:6][C:7]([OH:9])=[O:8])[CH:10]=[C:11]([F:13])[CH:12]=1

参加物

5

反応物 2

HCID 1118Sulfuric AcidHCID 5228103-(3,5-Difluorophenyl)acrylic acid

生成物 1

HCID 36694983-(3,5-Difluorophenyl)propionic acid収率 92.2%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 8028Tetrahydrofuran溶媒

実験手順

Hydrogenate a mixture of 3,5-difluorocinnamic acid (10.0 g, 54.3 mmol), 5% palladium on carbon (1.5 g), and concentrated sulfuric acid (10 ml) in tetrahydrofuran (195 ml) at 60 psi at room temperature overnight. After filtering the catalyst, dilute with ether, wash with water twice, dry over anhydrous sodium sulfate, and concentrate to obtain the title compound as clear colorless crystals (9.32 g, 92%). NMR (400 MHz, CDCl3): δ 2.67 (t, 2H), 2.94 (t, 2H), 6.65 (t, 1H), 6.74 (d, 2H).

後処理

  1. filtrationAfter filtering the catalyst
  2. additiondilute with ether
  3. washwash with water twice
  4. dry with materialdry over anhydrous sodium sulfate
  5. concentrationconcentrate

出典と根拠

ORDレコード
ord-53d1feeb0cf9479f8fdc097813fafe67
出典データセット
uspto-grants-2010_06
特許番号
US07728150B2

関連ノート

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