Nitric Acid → 3-Chloro-2,4-dimethylphenol

HRID 929095Notes

Reaction equation

HRID 929095 reaction equation
[N+]([O-])(O)=O.C(O)C.[C:8](=[O:10])=O.[Cl:11][C:12]1[C:17](C)=[CH:16][CH:15]=[CH:14][C:13]=1[CH3:19]>>[Cl:11][C:12]1[C:17]([CH3:16])=[C:8]([OH:10])[CH:15]=[CH:14][C:13]=1[CH3:19]

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 328851-Chloro-2,6-dimethylbenzene2×HCID 19604758Methanedione--ethanol (1/1)

Product 1

HCID 179117503-Chloro-2,4-dimethylphenol

Procedure

Nitration of 2-chloro-m-xylene. Nitric acid (90%, 50 mL) was cooled to −35° C. (ethanol-dry ice bath). 2-Chloro-m-xylene (10 mL) was added dropwise over 1 h keeping the temperature between −30° C. and −35° C. The reaction mixture was poured onto ice, stirred for 10 min, precipitate formed was collected by filtration, washed with water, dried. The crude product was purified on SiO2 (50 g), hexane-EtOAc (0 to 2% v/v). The product—yellow solid, 12.8 g, as a mixture of 2-chloro-1,3-dimethyl-4-nitro-benzene and chloro-1,3-dimethyl-5-nitro-benzene (4:1).

Workup

  1. customthe temperature between −30° C. and −35° C
  2. additionThe reaction mixture was poured onto ice
  3. customprecipitate formed
  4. filtrationwas collected by filtration
  5. washwashed with water
  6. customdried
  7. customThe crude product was purified on SiO2 (50 g), hexane-EtOAc (0 to 2% v/v)
  8. additionThe product—yellow solid, 12.8 g, as a mixture of 2-chloro-1,3-dimethyl-4-nitro-benzene and chloro-1,3-dimethyl-5-nitro-benzene (4:1)

Sources & evidence

ORD record
ord-b55747c1d5b6495a82483d550aff3fe0
Source dataset
uspto-grants-2016_03
Patent number
US09290503B2

Reaction notes

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