Lithium Hydroxide → 2-(3,4-Dimethoxyphenyl)-2-hydroxyacetic acid

HRID 1438176Notes

Reaction equation

HRID 1438176 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]([OH:16])[C:12]([O:14]C)=[O:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[Li+].[OH-]>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]([OH:16])[C:12]([OH:14])=[O:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 597469Methyl 2-(3,4-dimethoxyphenyl)-2-hydroxyacetate

Product 1

HCID 138548502-(3,4-Dimethoxyphenyl)-2-hydroxyacetic acidYield 100.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

137B (890 mg, 3.9 mmol) was dissolved in THF (6 mL). 1M LiOH (6 mL) was added, and the reaction was stirred at rt for 1 h. The solvent was removed under reduced pressure, and water (10 mL) was added. The solution was acidified with 1 N HCl, then extracted with ethyl acetate (3×20 mL). The organic layer was concentrated to provide 137C (830 mg, 100%). LC-MS: 235.11 (M+Na)+.

Workup

  1. customThe solvent was removed under reduced pressure, and water (10 mL)
  2. additionwas added
  3. extractionextracted with ethyl acetate (3×20 mL)
  4. concentrationThe organic layer was concentrated

Sources & evidence

ORD record
ord-c381dfea42b14638a8b0168500e31bbe
Source dataset
uspto-grants-2009_11
Patent number
US07622585B2

Reaction notes

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