Pyridine → Tert-butyl 2-methylpropanoate

HRID 636691Notes

Reaction equation

HRID 636691 reaction equation
[C:1](Cl)(=[O:5])[CH:2]([CH3:4])[CH3:3].N1C=CC=CC=1.[C:13]([OH:17])([CH3:16])([CH3:15])[CH3:14]>C(Cl)Cl>[C:1]([O:17][C:13]([CH3:16])([CH3:15])[CH3:14])(=[O:5])[CH:2]([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6386tert-ButanolHCID 62325Isobutyryl chloride

Product 1

HCID 519334Tert-butyl 2-methylpropanoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of isobutyryl chloride (47 g, 0.44 mol) in CH2Cl2 (75 ml) and tert-butanol (75 ml) at 0° C., pyridine (39.3 ml, 486 mmol) was added slowly by syringe. The mixture was allowed to warm to room temperature, stirred overnight, diluted with CH2Cl2 (400 ml) and washed with H2O, HCl (2N, two times), H2O (two times) and saturated NaHCO3. The organic phase was dried over MgSO4 and filtered. The filtrate was then concentrated under reduced pressure without heat. The resulting oil was simply distilled, collecting the fraction boiling at 128-129° C. to give tert-butyl isobutyrate, 21 (35.9 g, 56%).

Workup

  1. washwashed with H2O, HCl (2N, two times), H2O (two times) and saturated NaHCO3
  2. dry with materialThe organic phase was dried over MgSO4
  3. filtrationfiltered
  4. concentrationThe filtrate was then concentrated under reduced pressure
  5. temperaturewithout heat
  6. distillationThe resulting oil was simply distilled
  7. customcollecting the fraction boiling at 128-129° C.

Sources & evidence

ORD record
ord-ee2ca2f1cbae462582132114c9e9f5e7
Source dataset
uspto-grants-2001_02
Patent number
US06194448B1

Reaction notes

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