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

HRID 985581

반응식

HRID 985581 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

HCID 2285202-Tert-butyl-5-methyl-4-nitrosophenol수율 81.2%

시약·촉매·용매 1

HCID 962Water용매2회

반응 조건

온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-b1bf1b1509e24a439da990ed08530383
출처 데이터셋
uspto-grants-2005_03
특허 번호
US06872718B1

연결된 노트

불러오는 중…