Lithium Hydroxide → HCID 11344845, compound

HRID 921711Notes

Reaction equation

HRID 921711 reaction equation
[CH3:1][O:2][C:3]1[CH:16]=[CH:15][C:6]([CH2:7][O:8][C@@H:9]([CH3:14])[C:10]([O:12]C)=[O:11])=[CH:5][CH:4]=1.[OH-].[Li+]>C1COCC1.CO>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][O:8][C@@H:9]([CH3:14])[C:10]([OH:12])=[O:11])=[CH:15][CH:16]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 15907471HCID 15907471, compound

Product 1

HCID 11344845HCID 11344845, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (S)-methyl 2-((4-methoxybenzyl)oxy)propanoate (1 g, 4.46 mmol) in THF (20 mL) and MeOH (6 mL) at 0° C. was added lithium hydroxide (0.225 g, 9.38 mmol) and stirred for 3 h. Then warmed to room temperature in 30 min. After completion of starting material (by TLC), reaction mixture was concentrated and the resultant residue was taken EtOAc (100 ml), acidified by 1.5N HCl (up to pH 1) and extracted into EtOAc (2×100 ml). Combined organic extracts were dried over anhydrous Na2SO4, concentrated to give (S)-2-((4-methoxybenzyl)oxy)propanoic acid (0.6 g) was obtained as a gummy liquid.

Workup

  1. customAfter completion of starting material (by TLC), reaction mixture
  2. concentrationwas concentrated
  3. extractionextracted into EtOAc (2×100 ml)
  4. dry with materialCombined organic extracts were dried over anhydrous Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b56fd23f8895425daa5120c30f9920c0
Source dataset
uspto-grants-2016_03
Patent number
US09273057B2

Reaction notes

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