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

HRID 2103060Notes

Reaction equation

HRID 2103060 reaction equation
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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-9c00488efff84b0894fb74369e5bd5bb
Source dataset
uspto-grants-2009_08
Patent number
US07576094B2

Reaction notes

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