Water → 3,5-Dimethyl-4-nitrobenzoic acid

HRID 1282058

Reaction equation

HRID 1282058 reaction equation
[N+:1]([C:4]1[C:9]([CH3:10])=[CH:8]C(C)=[CH:6][C:5]=1[CH3:12])([O-:3])=[O:2].[CH:13]([OH:16])([CH3:15])C.[OH2:17]>C(O)(=O)C>[N+:1]([C:4]1[C:9]([CH3:10])=[CH:8][C:15]([C:13]([OH:16])=[O:17])=[CH:6][C:5]=1[CH3:12])([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 962WaterHCID 3776IsopropanolHCID 690512-Nitromesitylene

Product 1

HCID 2494133,5-Dimethyl-4-nitrobenzoic acid

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Conditions

Temperature
67.5 °C

Procedure

To a solution of chromic anhydride (40 g) in acetic acid (450 ml) was added a solution of nitromesitylene (20 g) in acetic acid (50 ml) at 65-70° C. over 20 min. This reaction mixture was stirred at 65-70° C. for 30 min and isopropyl alcohol (45 ml) was added. This reaction mixture was further stirred at 50° C. for 30 min. Water was added to the reaction mixture to make the total amount 500 ml and the mixture was ice-cooled. The precipitated crystals were collected by filtration to give the title compound (13 g) as pale-green crystals.

Workup

  1. stirringThis reaction mixture was further stirred at 50° C. for 30 min
  2. temperaturecooled
  3. filtrationThe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-e3d4f3486e11402b9c55c599b559a12e
Source dataset
uspto-grants-2002_09
Patent number
US06455528B1

Linked notes

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