Sulfuric Acid → 1-tert-Butyl-3-chloro-5-methylbenzene

HRID 1757236ノート

反応式

HRID 1757236 の反応式
[C:1]([C:5]1[CH:11]=[C:10]([CH3:12])[C:8](N)=[C:7]([Cl:13])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].S(=O)(=O)(O)O.N([O-])=O.[Na+]>C(O)C>[C:1]([C:5]1[CH:11]=[C:10]([CH3:12])[CH:8]=[C:7]([Cl:13])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

参加物

5

反応物 3

HCID 1118Sulfuric AcidHCID 19046432HCID 19046432、化合物HCID 23668193Sodium Nitrite

生成物 1

HCID 190464341-tert-Butyl-3-chloro-5-methylbenzene

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

4-t-Butyl-2-chloro-6-methylaniline (1.97 g) was dissolved in ethanol (50 ml); sulphuric acid (1.88 ml, conc.) was added dropwise and the resulting blue solution was heated at reflux. Sodium nitrite (1.72 g) was added portionwise over 30 min. The resulting mixture was heated at reflux for a further 30 min, then cooled and was poured onto ice-water and extracted with ether (2×50 ml). The ethereal extract was dried (MgSO4) and evaporated and the residue was purified on silica gel using hexane as eluant. This afforded the product as a colourless oil. 1H NMR (360 MHz, CDCl3) δ1.29 (9H, s, (CH3)3), 2.31 (3H, s, CH3), 6.98 (1H, brs, ArH), 7.05 (1H, brs, ArH), 7.15 (1H, brs, ArH). MS (CI-) m/z 181 (M+ -H, 100%).

後処理

  1. temperaturethe resulting blue solution was heated
  2. temperatureat reflux
  3. temperatureThe resulting mixture was heated
  4. temperatureat reflux for a further 30 min
  5. temperaturecooled
  6. additionwas poured onto ice-water
  7. extractionextracted with ether (2×50 ml)
  8. extractionThe ethereal extract
  9. dry with materialwas dried (MgSO4)
  10. customevaporated
  11. customthe residue was purified on silica gel

出典と根拠

ORDレコード
ord-f017a6a8fa5d433c89cda4bbb1e35736
出典データセット
uspto-grants-1995_08
特許番号
US05444074

反応ノート

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