Dimethylformamide → 4-(2-nitro-4,5-dimethylphenoxymethyl)-3-methylbenzoic Acid Methyl Ester

HRID 415703Notes

Reaction equation

HRID 415703 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([CH3:10])[C:7]([CH3:11])=[CH:6][C:5]=1[OH:12])([O-:3])=[O:2].CN(C=O)C.C(=O)([O-])[O-].[K+].[K+].[CH3:24][O:25][C:26](=[O:40])[C:27]1[CH:32]=[CH:31][C:30]([CH2:33]OS(C)(=O)=O)=[C:29]([CH3:39])[CH:28]=1>O>[CH3:24][O:25][C:26](=[O:40])[C:27]1[CH:32]=[CH:31][C:30]([CH2:33][O:12][C:5]2[CH:6]=[C:7]([CH3:11])[C:8]([CH3:10])=[CH:9][C:4]=2[N+:1]([O-:3])=[O:2])=[C:29]([CH3:39])[CH:28]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 3491174,5-Dimethyl-2-nitrophenolHCID 86591975Methyl 3-methyl-4-(((methylsulfonyl)oxy)methyl)benzoate

Product 1

HCID 588919084-(2-nitro-4,5-dimethylphenoxymethyl)-3-methylbenzoic Acid Methyl EsterYield 91.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

Under atmosphere of argon, a mixture of 2-nitro-4,5-dimethylphenol (4 g), DMF (100 ml), potassium carbonate (6.6 g) and 4-mesyloxymethyl-3-methylbenzoic acid methyl ester (6.8 g) were stirred for 15 minutes at 60° C. After the termination of reaction, the mixture was cooled and poured into iced water. The mixture was extracted with ethyl acetate-hexane. The organic layer was washed, dried, concentrated under reduced pressure to give the title compound (7.22 g) having the following physical data.

Workup

  1. customAfter the termination of reaction
  2. temperaturethe mixture was cooled
  3. extractionThe mixture was extracted with ethyl acetate-hexane
  4. washThe organic layer was washed
  5. customdried
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-84813aec54484b8b84aca97fe3f1c303
Source dataset
uspto-grants-2012_01
Patent number
US08088802B2

Reaction notes

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