Lithium Hydroxide → 3,5-Dicyanobenzoic acid

HRID 1397246ノート

反応式

HRID 1397246 の反応式
[C:1]([C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([C:13]#[N:14])[CH:12]=1)[C:6]([O:8]C)=[O:7])#[N:2].[Li+].[OH-]>C1COCC1.O>[C:13]([C:11]1[CH:10]=[C:5]([CH:4]=[C:3]([C:1]#[N:2])[CH:12]=1)[C:6]([OH:8])=[O:7])#[N:14]

参加物

4

反応物 2

HCID 3939Lithium HydroxideHCID 67325794HCID 67325794、化合物

生成物 1

HCID 219425673,5-Dicyanobenzoic acid収率 28%

試薬・触媒・溶媒 1

HCID 21881883Oxolane--water (1/1)溶媒

反応条件

温度
0 °C

実験手順

Methyl 3,5-dicyanobenzoate (400 mg, 2.1 mmol) was dissolved in THF—H2O (7:3 v/v, 30 mL), the solution was cooled to 0° C. and LiOH (51 mg, 2.1 mmol) was added. The reaction mixture was allowed to warm up to room temperature and stirred for 1 h. THF was removed under reduced pressure and the aqueous layer was washed with EtOAc, acidified to pH ˜2-3 using 1.5N HCl, and extracted with EtOAc. The organic layer was dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure. The crude product was purified by column chromatography (silica 60-120 mesh, eluent 20% MeOH in CHCl3) to get pure product 3,5-dicyanobenzoic acid (100 mg, yield 28%): 1H NMR (400 MHz, DMSO-d6) δ 8.53 (s, 1H), 8.50 (s, 2H). MS (ESI) m/z: Calculated for C9H4N2O2: 172.03. found: 171.2 (M−H)−.

後処理

  1. temperatureto warm up to room temperature
  2. customTHF was removed under reduced pressure
  3. washthe aqueous layer was washed with EtOAc
  4. extractionextracted with EtOAc
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. customthe solvent was removed under reduced pressure
  7. customThe crude product was purified by column chromatography (silica 60-120 mesh, eluent 20% MeOH in CHCl3)

出典と根拠

ORDレコード
ord-f8f7c14965f446248124a22b8cdbb3a6
出典データセット
uspto-grants-2014_12
特許番号
US08901156B2

反応ノート

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