Nitric Acid → 6-Methoxy-5-nitro-1,2,3,4-tetrahydronaphthalen-1-one

HRID 1357870

반응식

HRID 1357870 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[CH2:8][CH2:7][CH2:6]2.S(=O)(=O)(O)O.[N+:19]([O-:22])([OH:21])=[O:20]>CC(C)=O>[CH3:1][O:2][C:3]1[C:4]([N+:19]([O-:21])=[O:20])=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[CH2:8][CH2:7][CH2:6]2.[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[N+:19]([O-:22])=[O:20])[C:9](=[O:13])[CH2:8][CH2:7][CH2:6]2

참가 물질

6

반응물 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 141126-Methoxy-alpha-tetralone

생성물 2

HCID 130673376-Methoxy-5-nitro-1,2,3,4-tetrahydronaphthalen-1-oneHCID 13067338HCID 13067338, 화합물

시약·촉매·용매 1

HCID 180Acetone용매

반응 조건

온도
0 °C

실험 절차

To an ice-cold, stirred sloution of 6-methoxy-1-tetralone (17.6 g, 0.10 mol) in acetone (30 mL) was added dropwise a mixture of sulfuric acid (18 mL, 96.0%) and nitric acid (15 mL, 68.0-70.0%). After the addition was complete, the reaction was stirred at 0° C. for 6 hours, and TLC was employed to monitor the reaction progress. The reaction mixture was poured into ice-water, and the mixture was partitioned between CH2Cl2 (3*200 mL) and water (200 mL). The organic layer was washed by saturated NaHCO3 solution and water (200 mL each), dried over anhydrous sodium sulfate, and, after filtration, the organic layer was concentrated in vacuo to provide a yellow oil. 6-Methoxy-5-nitro-1-tetralone (7.74 g, 0.035 mol) and 6-methoxy-7-nitro-1-tetralone (6.63 g, 0.030 mol) was obtained after purification by column chromatography.

후처리

  1. additionwas added dropwise
  2. additionAfter the addition
  3. customthe mixture was partitioned between CH2Cl2 (3*200 mL) and water (200 mL)
  4. washThe organic layer was washed by saturated NaHCO3 solution and water (200 mL each)
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationafter filtration
  7. concentrationthe organic layer was concentrated in vacuo
  8. customto provide a yellow oil

출처 및 근거

ORD 기록
ord-08a49c84b1564e4e88040a767e1f03c2
출처 데이터셋
uspto-grants-2003_07
특허 번호
US06593374B2

연결된 노트

불러오는 중…