Hydrochloric Acid → 2(3H)-Benzofuranone, hexahydro-

HRID 2303448ノート

反応式

HRID 2303448 の反応式
O=[C:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[CH2:8][C:9]([OH:11])=[O:10].[BH4-].[Na+].Cl>[OH-].[Na+]>[O:11]1[CH:2]2[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]2[CH2:8][C:9]1=[O:10]

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 109207542-Oxocyclohexylacetic acid

生成物 1

HCID 953912(3H)-Benzofuranone, hexahydro-

試薬・触媒・溶媒 1

HCID 14798Sodium Hydroxide溶媒2 回

反応条件

温度
0 °C

実験手順

2-Oxocyclohexylacetic acid (31.2 g, 200 mmol) is dissolved in 125 ml of 0.2 N aqueous sodium hydroxide solution and, at room temperature, added dropwise to a solution of sodium borohydride (18.9 g, 500 mmol) in 150 ml of 0.2 N aqueous sodium hydroxide solution. The mixture is stirred for 20 h and then cooled to 0° C. and carefully acidified with 6 N HCl. The strongly acidic solution is then heated at 100° C. for 30 min and subsequently stirred overnight. The cold mixture is then extracted with MTBE, and the combined ether phases are washed with 5% strength sodium carbonate solution and sat. NaCl solution, dried over magnesium sulphate, filtered and concentrated. Purification is carried out by distillation (b.p.: 75° C./0.01 mm). Yield: 22.9 g (81.7%). MS (CI): m/e=141 [M+H+]

後処理

  1. temperatureThe strongly acidic solution is then heated at 100° C. for 30 min and subsequently stirred overnight
  2. extractionThe cold mixture is then extracted with MTBE
  3. washthe combined ether phases are washed with 5% strength sodium carbonate solution and sat. NaCl solution
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification
  8. distillationis carried out by distillation (b.p.: 75° C./0.01 mm)

出典と根拠

ORDレコード
ord-4fc3c65af649429ea5b88d84146e879b
出典データセット
uspto-grants-2002_08
特許番号
US06433004B1

反応ノート

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