tert-Butanol → Tert-butyl acetoacetate

HRID 1031228Notes

Reaction equation

HRID 1031228 reaction equation
[CH2:1]=[C:2]1[O:6][C:4](=[O:5])[CH2:3]1.[C:7]([OH:11])([CH3:10])([CH3:9])[CH3:8]>CN(C)C1C=CN=CC=1>[O:6]=[C:2]([CH3:1])[CH2:3][C:4]([O:11][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5]

Participants

4

Reactant 2

HCID 6386tert-ButanolHCID 12661Diketene

Product 1

HCID 15538Tert-butyl acetoacetateYield 98.6%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

To a mixture of tert-butyl alcohol [74.1 g] and 4-(dimethylamino)pyridine [0.61 g] was added dropwise diketene [84.1 g] at 50° to 60° C. in the course of one hour while stirring. The stirring was continued for one further hour at 30° to 50° C. to obtain a colorless and clear reaction mixture, which was subjected to distillation under reduced pressure (b.p. 85° C./20 mmHg) to yield tert-butyl 3-oxobutyrate [156 g] as an oily product. The yield was 98.6%. NMR(CDCl3): δ3.34(2H,s), 2.25(3H,s), 1.47(9H,s)ppm .

Workup

  1. customwas continued for one further hour at 30° to 50° C.
  2. customto obtain a colorless and clear reaction mixture, which
  3. distillationwas subjected to distillation under reduced pressure (b.p. 85° C./20 mmHg)

Sources & evidence

ORD record
ord-9774fbd73d6c4f79babdfcfe2721efd7
Source dataset
uspto-grants-1992_04
Patent number
US05109131

Reaction notes

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