Sodium Cyanide → Methyl 4-(cyanomethyl)benzoate

HRID 8910

反応式

HRID 8910 の反応式
Br[CH2:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=1.[C-:13]#[N:14].[Na+]>[Br-].C([N+](C)(C)C)CCCCCCCCCCCCCCC.C1C=CC=CC=1.O>[CH3:10][O:9][C:7](=[O:8])[C:6]1[CH:11]=[CH:12][C:3]([CH2:2][C:13]#[N:14])=[CH:4][CH:5]=1

参加物

5

反応物 2

HCID 8929Sodium CyanideHCID 256687Methyl 4-(bromomethyl)benzoate

生成物 1

HCID 848548Methyl 4-(cyanomethyl)benzoate収率 60.1%

試薬・触媒・溶媒 2

HCID 5974Hexadecyltrimethylammonium Bromide触媒HCID 22272175Benzene--water (1/1)溶媒

実験手順

A mixture of methyl 4-(bromomethyl)benzoate (10.09 g, 44.05 mmol), sodium cyanide (6.42 g, 131 mmol) and cetyltrimethylammonium bromide (1.59 g, 4.36 mmol) in benzene/water (2:1, 187.5 mL) was heated at reflux for 5 h then extracted with CH2Cl2 3×50 mL). The organic extracts were dried (MgSO4), filtered and concentrated under reduced pressure. Purification of the crude material by chromatography on silica gel (35% EtOAc/hexanes) gave 4-cyanomethyl-benzoic acid methyl ester as a colourless solid (4.64 g, 60%). 1H NMR (CDCl3) δ 3.82 (s, 2H), 3.93 (s, 3H), 7.42 (d, 2H, J=9 Hz), 8.06 (d, 2H, J=9 Hz).

後処理

  1. temperaturewas heated
  2. temperatureat reflux for 5 h
  3. extractionthen extracted with CH2Cl2 3×50 mL)
  4. dry with materialThe organic extracts were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customPurification of the crude material by chromatography on silica gel (35% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-8bd81bc8e07d4d19bf9f7f99862fa9cd
出典データセット
uspto-grants-2006_08
特許番号
US07091217B2

関連ノート

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