Sulfuric Acid → 4-Nitro-3-hydroxycinnamic acid

HRID 568052노트

반응식

HRID 568052 반응식
[OH:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[CH:5]=[CH:6][C:7]([OH:9])=[O:8].[N+:13]([O-])([O-:15])=[O:14].[Na+].S(=O)(=O)(O)O.N([O-])=O.[Na+]>C(Cl)Cl>[N+:13]([C:12]1[CH:11]=[CH:10][C:4]([CH:5]=[CH:6][C:7]([OH:9])=[O:8])=[CH:3][C:2]=1[OH:1])([O-:15])=[O:14]

참가 물질

6

반응물 4

HCID 1118Sulfuric AcidHCID 114963-(3-Hydroxyphenyl)-2-propenoic acidHCID 24268Sodium NitrateHCID 23668193Sodium Nitrite

생성물 1

HCID 534017114-Nitro-3-hydroxycinnamic acid수율 26.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

3-Hydroxycinnamic acid (3.00 g, 18.3 mmol) was dissolved in methylene chloride(40 mL) followed by the addition of sodium nitrate (1.70 g, 26.1 mmol). The addition of sulfuric acid (25 mL/3M) was then made, followed by addition of a catalytic amount of sodium nitrite. The mixture was allowed to stir. After 24 hours, the reaction mixture was diluted with methylene chloride and extracted with water. The organic layer was dried over MgSO4 and filtered. The solvent was evaporated and chromatography of the resulting solid on silica gel (4% MeOH/CH2Cl2) gave the desired product(1.0 g, 26%). 1H NMR (CD3COCD3): δ 8.07 (d, 1H), 7.69 (d, 1H), 7.51 (s, 1H), 7.46 (d, 2H), 6.75 (d,1H).

후처리

  1. extractionextracted with water
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. customThe solvent was evaporated

출처 및 근거

ORD 기록
ord-a4c2a049e7eb482c9790a39156456ba0
출처 데이터셋
uspto-grants-2001_01
특허 번호
US06180675B2

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