Pyridine → 1,1-Dimethylethyl 4-methylbenzoate

HRID 234492

Reaction equation

HRID 234492 reaction equation
[C:1]([OH:5])([CH3:4])([CH3:3])[CH3:2].N1C=CC=CC=1.[C:12]1([CH3:21])[CH:17]=[CH:16][C:15]([C:18](Cl)=[O:19])=[CH:14][CH:13]=1>O>[CH3:21][C:12]1[CH:17]=[CH:16][C:15]([C:18]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:19])=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 6386tert-ButanolHCID 134054-Methylbenzoyl Chloride

Product 1

HCID 116297491,1-Dimethylethyl 4-methylbenzoateYield 80.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

37 g of tert-butanol and then 26 ml of pyridine are added to 39.04 g of p-toluoyl chloride and the reaction mixture is refluxed for 3 hours. After cooling, it is poured into water, extracted with AcOEt, washed with a 1N solution of HCl and then with a 5% solution of sodium hydrogencarbonate, dried over sodium sulfate and evaporated under vacuum. The residue is chromatographed on silica using hexane and then a hexane/DCM mixture (80/20; v/v) as the eluent to give 38.9 g of the expected product, which is used as such in the next step.

Workup

  1. temperaturethe reaction mixture is refluxed for 3 hours
  2. temperatureAfter cooling
  3. extractionextracted with AcOEt
  4. washwashed with a 1N solution of HCl
  5. dry with materialwith a 5% solution of sodium hydrogencarbonate, dried over sodium sulfate
  6. customevaporated under vacuum
  7. customThe residue is chromatographed on silica

Sources & evidence

ORD record
ord-322a45395b44461bbbe7c7c16a2bbff1
Source dataset
uspto-grants-1997_01
Patent number
US05594023

Linked notes

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