Nitric Acid → 2,3,6-Trimethyl-4-nitrophenol

HRID 2103060ノート

反応式

HRID 2103060 の反応式
ClC1C=CC(N2[C:17]3[C:12](=[C:13]([CH3:21])[C:14]([OH:20])=[C:15]([CH3:19])[C:16]=3C)[CH2:11]C3(CCC3)C2)=CC=1.[N+:25]([O-:28])(O)=[O:26]>C(O)(=O)C>[CH3:21][C:13]1[C:12]([CH3:11])=[C:17]([N+:25]([O-:28])=[O:26])[CH:16]=[C:15]([CH3:19])[C:14]=1[OH:20]

参加物

4

反応物 2

HCID 944Nitric AcidHCID 116242921'-(4-Chlorophenyl)-5',7',8'-trimethyl-1',4'-dihydro-2'H-spiro[cyclobutane-1,3'-quinolin]-6'-ol

生成物 1

HCID 133312472,3,6-Trimethyl-4-nitrophenol

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒2 回

実験手順

2,3,6-trimethyl phenol 1 (19.1 g) was dissolved in acetic acid (190 mL). This solution was added to an acetic acid solution of HNO3 (150 mL, 1M) at room temperature in 4.5 hours. After another 0.5 hour, the mixture was evaporated, and the residue was taken up by EtOAc (350 mL). This solution was washed with water (150 mL×2), and brine (150 mL), dried and evaporated. Elution on a silica column (Hexane: EtOAc, 5:1-5:2), gave 2,3,6-trimethyl-4-nitrophenol (7.56 g), as a yellow solid. 1H-NMR, (300 MHz, CDCl3) δ=7.61 6, (br s, 1H), 2.432 (s, 3H), 2.275 (s, 3H), 2.242 (s, 3H) ppm.

後処理

  1. customthe mixture was evaporated
  2. washThis solution was washed with water (150 mL×2), and brine (150 mL)
  3. customdried
  4. customevaporated
  5. washElution on a silica column (Hexane: EtOAc, 5:1-5:2)

出典と根拠

ORDレコード
ord-9c00488efff84b0894fb74369e5bd5bb
出典データセット
uspto-grants-2009_08
特許番号
US07576094B2

反応ノート

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