Sodium Hydroxide → (S)-3-(Benzyloxy)butanoic acid

HRID 238944Notes

Reaction equation

HRID 238944 reaction equation
C([O:3][C:4](=[O:18])[CH:5](CC)[C@@H:6]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH3:7])C.[OH-].[Na+]>O1CCOCC1>[CH2:9]([O:8][C@@H:6]([CH3:7])[CH2:5][C:4]([OH:18])=[O:3])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67361131ethyl (3S)-3-(benzyloxy)butanoic acid ethyl ester

Product 1

HCID 11845529(S)-3-(Benzyloxy)butanoic acidYield 96.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of the above ethyl (3S)-3-(benzyloxy)butanoic acid ethyl ester (339 g) in 1,4-dioxane (1.5 L), 2N aqueous sodium hydroxide solution (0.75 L, 1.5 mol) was added, and the mixture was stirred at room temperature for 3 hours. After the reaction, the solvent was distilled off under reduced pressure, and after the aqueous phase was washed with diethyl ether, concentrated hydrochloric acid (0.14 L) was added to acidify it. After it was extracted with ethyl acetate, it was successively washed with water and saturated brine, and then it was dried with sodium sulfate and the solvent was distilled off under reduced pressure to give (3S)-3-(benzyloxy)butanoic acid (254 g) as a mixture. The present compound was used for the subsequent reaction without further purification.

Workup

  1. customAfter the reaction
  2. distillationthe solvent was distilled off under reduced pressure
  3. washafter the aqueous phase was washed with diethyl ether, concentrated hydrochloric acid (0.14 L)
  4. additionwas added
  5. extractionAfter it was extracted with ethyl acetate, it
  6. washwas successively washed with water and saturated brine
  7. dry with materialit was dried with sodium sulfate
  8. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-b4e1e16c6135455ba695555feed1f8e0
Source dataset
uspto-grants-2014_02
Patent number
US08642640B2

Reaction notes

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