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

HRID 1757236노트

반응식

HRID 1757236 반응식
[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]

참가 물질

5

반응물 3

HCID 1118Sulfuric AcidHCID 19046432HCID 19046432, 화합물HCID 23668193Sodium Nitrite

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-f017a6a8fa5d433c89cda4bbb1e35736
출처 데이터셋
uspto-grants-1995_08
특허 번호
US05444074

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