Potassium Hydroxide → HCID 23370057, compound

HRID 1900908Notes

Reaction equation

HRID 1900908 reaction equation
[C:1]([O:5][C:6]([CH:8]([CH2:16][CH2:17][O:18][CH2:19][CH3:20])[C:9]([O:11]C(C)(C)C)=[O:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[K+]>O1CCOCC1.O>[C:1]([O:5][C:6]([CH:8]([CH2:16][CH2:17][O:18][CH2:19][CH3:20])[C:9]([OH:11])=[O:10])=[O:7])([CH3:3])([CH3:2])[CH3:4]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 23370044HCID 23370044, compound

Product 1

HCID 23370057HCID 23370057, compoundYield 26.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of the product from step (a) (5 g) in dioxane (25 ml) was added a solution of potassium hydroxide (1 g) in water (20 ml). The cloudy reaction mixture was heated to reflux for 5.5 hours and then evaporated to dryness. The residue was dissolved in water, washed with ether, and acidified to pH 4 with conc. HCl. The mixture was extracted thoroughly with ethyl acetate and the combined extracts were washed with brine, dried (MgSO4) and evaporated to give 2-t-butoxycarbonyl-4-ethoxybutyric acid (1.06 g) as a yellow oil: NMR Spectrum (CDCl3) 1.19 (3H, t), 1.49 (9H, s), 2.19 (2H, m), 3.50 (5H, m); Mass Spectrum m/Z 233 (M+H)+.

Workup

  1. customThe cloudy reaction mixture
  2. temperaturewas heated
  3. temperatureto reflux for 5.5 hours
  4. customevaporated to dryness
  5. dissolutionThe residue was dissolved in water
  6. washwashed with ether
  7. extractionThe mixture was extracted thoroughly with ethyl acetate
  8. washthe combined extracts were washed with brine
  9. dry with materialdried (MgSO4)
  10. customevaporated

Sources & evidence

ORD record
ord-1f11588eb01d4c3bbcec4f1ba8ab1800
Source dataset
uspto-grants-1996_11
Patent number
US05576334

Reaction notes

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