Sodium Cyanide → (4-Methoxyphenyl)glycolonitrile

HRID 37624

反応式

HRID 37624 の反応式
S(=O)(O)[O-].[Na+].[CH:6](=[O:15])[C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=1.[C-:16]#[N:17].[Na+].COC(C)(C)C>O>[CH3:14][O:13][C:10]1[CH:11]=[CH:12][C:7]([CH:6]([OH:15])[C:16]#[N:17])=[CH:8][CH:9]=1

参加物

6

反応物 4

HCID 8929Sodium CyanideHCID 15413tert-Butyl methyl etherHCID 312444-MethoxybenzaldehydeHCID 23665763Sodium Bisulfite

生成物 1

HCID 36571(4-Methoxyphenyl)glycolonitrile

試薬・触媒・溶媒 1

HCID 962Water溶媒2 回

反応条件

温度
40 °C

実験手順

Water (720 ml), sodium bisulfite (81 g, 0.775 mol, 1.2 equiv) and p-anisaldehyde (88 g, 0.646 mol, 1.0 equiv) are combined, warmed to 40° C. and stirred for 3 hrs. The slurry is cooled to 5° C., and sodium cyanide (35 g, 0.711 mol, 1.1 equiv) in 140 ml water is added. The reaction is stirred for 2 hrs. at 5° C., then warmed to room temperature, and methyl-t-butyl ether (MTBE) (400 ml) added. The layers are separated after a brief stir, and the aqueous phase re-extracted with MTBE (100 ml). The combined organic layers were dried (MgSO4), and concentrated to an oil, which was seeded to afford product: 69.5 g, 65.9%. The material can be recrystallized from toluene (3 ml per g substrate, heat to 35° C., cool to 5° C., 90% recovery).

後処理

  1. temperatureThe slurry is cooled to 5° C.
  2. stirringThe reaction is stirred for 2 hrs
  3. temperatureat 5° C., then warmed to room temperature
  4. customThe layers are separated after a brief stir
  5. extractionthe aqueous phase re-extracted with MTBE (100 ml)
  6. dry with materialThe combined organic layers were dried (MgSO4)
  7. concentrationconcentrated to an oil, which
  8. customto afford product
  9. customThe material can be recrystallized from toluene (3 ml per g substrate, heat to 35° C., cool to 5° C., 90% recovery)

出典と根拠

ORDレコード
ord-2c85248ab63642ada26290d14a983e6a
出典データセット
uspto-grants-1995_05
特許番号
US05420349

関連ノート

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