Pyridine → 1,1-Dimethylethyl 4-methylbenzoate

HRID 1913768Notes

Reaction equation

HRID 1913768 reaction equation
[C:1]1([CH3:10])[CH:6]=[CH:5][C:4]([C:7](Cl)=[O:8])=[CH:3][CH:2]=1.[C:11]([OH:15])([CH3:14])([CH3:13])[CH3:12].N1C=CC=CC=1>O>[CH3:10][C:1]1[CH:6]=[CH:5][C:4]([C:7]([O:15][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:8])=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 6386tert-ButanolHCID 134054-Methylbenzoyl Chloride

Product 1

HCID 116297491,1-Dimethylethyl 4-methylbenzoateYield 62.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

8.55 ml (64.69 mmol) of 4-toluoyl chloride are added dropwise to 10.52 ml (109.96 mmol) of tert-butanol and 10.46 ml (129.37 mmol) of pyridine while cooling in ice. The mixture is stirred at room temperature for 12 hours. After reaction is complete, water is added and the mixture is extracted with ethyl acetate. The organic phase is washed successively with sodium bicarbonate solution, water and sodium chloride solution, dried over sodium sulphate and evaporated. The resulting residue is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 50:1). 7.76 g (40.36 mmol, 62% yield) of the title compound are obtained as a colourless oil.

Workup

  1. temperaturewhile cooling in ice
  2. customAfter reaction
  3. extractionthe mixture is extracted with ethyl acetate
  4. washThe organic phase is washed successively with sodium bicarbonate solution, water and sodium chloride solution
  5. dry with materialdried over sodium sulphate
  6. customevaporated
  7. customThe resulting residue is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 50:1)

Sources & evidence

ORD record
ord-695c8f519cac4c90a4f4d514b32c3bc9
Source dataset
uspto-grants-2013_12
Patent number
US08609727B2

Reaction notes

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