Dichloromethane → Phenol, 2-chloro-3-nitro-

HRID 36865

反応式

HRID 36865 の反応式
[N+:1]([C:4]1[CH:5]=[C:6]([OH:10])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[Cl:11]([O-])(=O)=O.[K+].ClCCl>Cl.O>[Cl:11][C:5]1[C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=[CH:7][C:6]=1[OH:10]

参加物

6

反応物 3

HCID 6344DichloromethaneHCID 111373-NitrophenolHCID 6426889Potassium Chlorate

生成物 1

HCID 3013917Phenol, 2-chloro-3-nitro-収率 64.3%

試薬・触媒・溶媒 2

HCID 313Hydrochloric Acid溶媒HCID 962Water溶媒

反応条件

温度
15 °C

実験手順

73 g (0.52 mol) of 3-nitrophenol are dissolved in 2 liters-of 6N hydrochloric acid while heating. The mixture is cooled in an ice bath to 28°-30° C. 32 g (0.26 mol) of potassium chlorate in 500 ml of water are added over 1.5 hours and then, at the end of the addition, the mixture is left stirring for 30 minutes at 28°-30° C. The mixture is cooled to 15° C. and 1 liter of dichloromethane is added. The layers are separated and the organic phase is washed with water. The organic phase is dried and evaporated. The residue is purified by chromatography on a column of silica gel, eluting with a dichloromethane/methanol (80/20) mixture. Recrystallization is carried out from toluene. 29 g of product are obtained.

後処理

  1. temperaturewhile heating
  2. temperatureThe mixture is cooled in an ice bath to 28°-30° C
  3. additionat the end of the addition
  4. waitthe mixture is left
  5. customThe layers are separated
  6. washthe organic phase is washed with water
  7. customThe organic phase is dried
  8. customevaporated
  9. customThe residue is purified by chromatography on a column of silica gel
  10. washeluting with a dichloromethane/methanol (80/20) mixture
  11. customRecrystallization

出典と根拠

ORDレコード
ord-945c0e5684024f81beb47d87c2e71169
出典データセット
uspto-grants-1995_05
特許番号
US05418241

関連ノート

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