Sodium Hydroxide → 2-Tert-butyl-5-methyl-4-oxazoleacetic acid

HRID 2215191Notes

Reaction equation

HRID 2215191 reaction equation
[C:1]([C:5]1[O:6][C:7]([CH3:13])=[C:8]([CH2:10][C:11]#N)[N:9]=1)([CH3:4])([CH3:3])[CH3:2].[OH-:14].[Na+].CCO.[OH2:19]>>[C:1]([C:5]1[O:6][C:7]([CH3:13])=[C:8]([CH2:10][C:11]([OH:19])=[O:14])[N:9]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 11506550(2-tert-Butyl-5-methyl-oxazol-4-yl)-acetonitrileHCID 19096565Water ethanol

Product 1

HCID 132829732-Tert-butyl-5-methyl-4-oxazoleacetic acid

Procedure

13.19 g of the above prepared (2-tert-butyl-5-methyl-oxazol-4-yl)-acetonitrile (74.0 mmol) was dissolved in 170 ml EtOH/water=1/1 and treated with 5 eq. of NaOH-pellets (14.8 g). Hydrolysis was allowed to proceed over night at 65° C. Pouring onto crashed ice/HCl, twofold extraction with AcOEt, washing with water, drying over sodium sulfate, followed by evaporation of the solvents, yielded 13.77 g of the title acid as waxy solid.

Workup

  1. customHydrolysis
  2. waitto proceed over night at 65° C
  3. additionPouring
  4. extractionice/HCl, twofold extraction with AcOEt
  5. washwashing with water
  6. dry with materialdrying over sodium sulfate
  7. customfollowed by evaporation of the solvents
  8. customyielded 13.77 g of the title acid as waxy solid

Sources & evidence

ORD record
ord-a8a007a4e758478887004802d8a8d43f
Source dataset
uspto-grants-2006_09
Patent number
US07109225B2

Reaction notes

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