tert-Butanol → Tert-butyl 4-methyl-3-nitrobenzoate

HRID 1893530Notes

Reaction equation

HRID 1893530 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].CCN=C=NCCCN(C)C.[C:25](O)([CH3:28])([CH3:27])[CH3:26]>CN(C)C1C=CN=CC=1.ClCCl>[C:25]([O:7][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:2]([CH3:1])=[C:3]([N+:11]([O-:13])=[O:12])[CH:4]=1)([CH3:28])([CH3:27])[CH3:26]

Participants

6

Reactant 3

HCID 6386tert-ButanolHCID 73194-Methyl-3-nitrobenzoic acidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide

Product 1

HCID 22451886Tert-butyl 4-methyl-3-nitrobenzoateYield 93%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

4-methyl-3-nitrobenzoic acid (40.0 g, 221 mmol), 4-dimethylaminopyridine (54.5 g, 446 mmol) and WSC (84.4 g, 440 mmol) were dissolved in dichloromethane (450 ml). tert-Butanol (34.4 g, 464 mmol) was added with stirring at room temperature, and the mixture was stirred at the same temperature overnight. The reaction mixture was concentrated under reduced pressure, and diluted with ethyl acetate-hexane=1:1 mixed solvent (500 ml). The organic layer was washed with water, 10% aqueous citric acid solution, saturated aqueous sodium hydrogen carbonate and saturated brine, and dried over anhydrous magnesium sulfate. The insoluble material was filtered off, and the solution was concentrated under reduced pressure to give the title compound (48.7 g, yield 93%) as a pale-yellow solid.

Workup

  1. stirringthe mixture was stirred at the same temperature overnight
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additiondiluted with ethyl acetate-hexane=1:1 mixed solvent (500 ml)
  4. washThe organic layer was washed with water, 10% aqueous citric acid solution, saturated aqueous sodium hydrogen carbonate and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationThe insoluble material was filtered off
  7. concentrationthe solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-c67d08129ed14d41950db96b230ef273
Source dataset
uspto-grants-2013_08
Patent number
US08513235B2

Reaction notes

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