Nitric Acid → 2,3-Dimethoxy-6-nitrophenol

HRID 1250338ノート

反応式

HRID 1250338 の反応式
[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][CH:6]=[CH:5][C:4]=1[OH:11].[N+:12]([O-])([OH:14])=[O:13].C1(O)C=CC=CC=1.C(=O)(O)[O-].[Na+]>C(O)(=O)C.O>[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][CH:6]=[C:5]([N+:12]([O-:14])=[O:13])[C:4]=1[OH:11]

参加物

7

反応物 4

HCID 944Nitric AcidHCID 996PhenolHCID 788282,3-DimethoxyphenolHCID 516892Sodium Bicarbonate

生成物 1

HCID 3193242,3-Dimethoxy-6-nitrophenol

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 962Water溶媒2 回

反応条件

温度
5 °C

実験手順

2,3-Dimethoxyphenol (79) (5.00 g, 0.032 mol) was dissolved in glacial acetic acid (50 ml) and the resultant, stirred solution was cooled to 5° C. A cooled (5° C.) mixture of concentrated nitric acid (10 ml) and water (10 ml) was added in one portion to the phenol solution which immediately turned dark red-brown. The mixture was stirred for a further minute and poured into water (200 ml), this solution was neutralised with saturated sodium bicarbonate solution until all effervescense had ceased. The resultant yellow solution was extracted with several portions of diethyl ether until the ether remained almost colourless. The combined extracts were washed with water until the water remained almost colourless, dried (MgSO4) and the ether evaporated off in vacuo to leave a brown oil. This was purified by column chromatography (10% petrol/dichloromethane) to give a bright yellow solid.

後処理

  1. temperatureA cooled
  2. stirringThe mixture was stirred for a further minute
  3. extractionThe resultant yellow solution was extracted with several portions of diethyl ether until the ether
  4. washThe combined extracts were washed with water until the water
  5. dry with materialdried (MgSO4)
  6. customthe ether evaporated off in vacuo
  7. customto leave a brown oil
  8. customThis was purified by column chromatography (10% petrol/dichloromethane)
  9. customto give a bright yellow solid

出典と根拠

ORDレコード
ord-31f6d226d57f4957a24f839a5d8bbf21
出典データセット
uspto-grants-2002_01
特許番号
US06337420B1

反応ノート

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