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

HRID 2361151Notes

Reaction equation

HRID 2361151 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-decb2a4842e1489f8f23990969193af8
Source dataset
uspto-grants-2014_04
Patent number
US08686005B2

Reaction notes

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