Sulfuric Acid → 3-Nitro-2-hydroxycinnamic acid

HRID 612708

反応式

HRID 612708 の反応式
[OH:1][C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[CH:4]=[CH:5][C:6]([OH:8])=[O:7].[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[C:2]([OH:1])=[C:3]([CH:9]=[CH:10][CH:11]=1)[CH:4]=[CH:5][C:6]([OH:8])=[O:7])([O-:15])=[O:14]

参加物

6

反応物 4

HCID 1118Sulfuric AcidHCID 119683-(2-Hydroxyphenyl)-2-propenoic acidHCID 24268Sodium NitrateHCID 23668193Sodium Nitrite

生成物 1

HCID 534016493-Nitro-2-hydroxycinnamic acid収率 52.3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

2-Hydroxycinnamic acid (3.00 g, 18.3 mmol) was dissolved in methylene chloride (40 mL) followed by the addition of sodium nitrate (2.21 g, 26.1 mmol). The addition of sulfuric acid (30 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 (2.0 g, 52%). 1H NMR (CD3COCD3): δ8.21 (d, 1H), 8.16 (d, 1H), 8.05 (d, 1H), 7.19 (t, 1H), 6.72 (d, 1H).

後処理

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

出典と根拠

ORDレコード
ord-53a2a58c9f704848b5f5087c7f3a766f
出典データセット
uspto-grants-1999_12
特許番号
US06005008

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