Hydrochloric Acid → Tert-butyl 2-methylpropanoate

HRID 353163Notes

Reaction equation

HRID 353163 reaction equation
[C:1]([OH:5])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[C:13](Cl)(=[O:17])[CH:14]([CH3:16])[CH3:15].Cl>CN(C1C=CN=CC=1)C.ClCCl>[CH3:15][CH:14]([CH3:16])[C:13]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:17]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6386tert-ButanolHCID 8471TriethylamineHCID 62325Isobutyryl chloride

Product 1

HCID 519334Tert-butyl 2-methylpropanoateYield 48,370%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

With ice-cooling, a solution of 73.0 g (0.985 mol) of tert-butanol, 190 g (1.877 mol) of triethylamine and 0.573 g (0.0047 mol) of DMAP in 750 ml of dichloromethane is treated with a solution of 100 g (0.939 mmol) of isobutyryl chloride in 150 ml of dichloromethane, and the mixture is then stirred overnight. 500 ml of 2 M hydrochloric acid are then added, the aqueous phase is extracted with dichloromethane and the combined organic phases are washed with water, sat. NaHCO3 solution and sat. NaCl solution, dried over sodium sulphate and concentrated. Distillative purification of the crude product gives 65.5 g (48%) of tert-butyl 2-methylpropionate.

Workup

  1. temperatureWith ice-cooling
  2. extractionthe aqueous phase is extracted with dichloromethane
  3. washthe combined organic phases are washed with water, sat. NaHCO3 solution and sat. NaCl solution
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated
  6. distillationDistillative purification of the crude product

Sources & evidence

ORD record
ord-b43a7fb666be40fd9d751313ccf0aa09
Source dataset
uspto-grants-2004_06
Patent number
US06750236B2

Reaction notes

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