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

HRID 2103060Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2103060
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]

Komponenten

4

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel2×

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-9c00488efff84b0894fb74369e5bd5bb
Quelldatensatz
uspto-grants-2009_08
Patentnummer
US07576094B2

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