Hydrochloric Acid → 2-Tert-butyl-5-methyl-4-nitrosophenol

HRID 985581

反応式

HRID 985581 の反応式
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][C:6]=1[OH:12])([CH3:4])([CH3:3])[CH3:2].C(O)C.Cl.[N:17]([O-])=[O:18].[Na+]>O>[C:1]([C:5]1[CH:10]=[C:9]([N:17]=[O:18])[C:8]([CH3:11])=[CH:7][C:6]=1[OH:12])([CH3:4])([CH3:3])[CH3:2]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 69376-tert-Butyl-m-cresolHCID 23668193Sodium Nitrite

生成物 1

HCID 2285202-Tert-butyl-5-methyl-4-nitrosophenol収率 81.2%

試薬・触媒・溶媒 1

HCID 962Water溶媒2 回

反応条件

温度
0 °C

実験手順

To a solution of 2-(tert-butyl)-5-methylphenol (32.9 g, 0.2 mol) in water:ethanol (300 ml, 2:1) was added concentrated hydrochloric acid (20 ml, 0.24 mol) and then cooled to 0° C. To the solution was added dropwise a solution of sodium nitrite (14.5 g, 0.21 mol) in water (40 ml) over 30 minutes. After completing the dropwise addition, the mixture was stirred at the same temperature for 2 hours. The precipitated crystals were collected by a filtration, and washed with a cold water. The resultant crystal was dissolved in an ethyl acetate:THF (9:1) solution, washed with saturated brine, dried over sodium sulfate, and purified by silica gel column chromatography on a small amount of silica gel which was eluted with ethyl acetate. After the solvent was removed under reduced pressure, the residue was suspended in hexane and the crystals were collected by filtration to obtain 31.4 g of the title compound.

後処理

  1. additionthe dropwise addition
  2. filtrationThe precipitated crystals were collected by a filtration
  3. washwashed with a cold water
  4. dissolutionThe resultant crystal was dissolved in an ethyl acetate:THF (9:1) solution
  5. washwashed with saturated brine
  6. dry with materialdried over sodium sulfate
  7. custompurified by silica gel column chromatography on a small amount of silica gel which
  8. washwas eluted with ethyl acetate
  9. customAfter the solvent was removed under reduced pressure
  10. filtrationthe crystals were collected by filtration

出典と根拠

ORDレコード
ord-b1bf1b1509e24a439da990ed08530383
出典データセット
uspto-grants-2005_03
特許番号
US06872718B1

関連ノート

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