Lithium Hydroxide → HCID 18443662, compound

HRID 459148

Reaction equation

HRID 459148 reaction equation
[OH-].[Li+].C[O:4][C:5](=[O:19])[CH:6]([O:17][CH3:18])[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[C:10]([O:15][CH3:16])[CH:9]=1>C1COCC1>[OH:14][C:11]1[CH:12]=[CH:13][C:8]([CH2:7][CH:6]([O:17][CH3:18])[C:5]([OH:19])=[O:4])=[CH:9][C:10]=1[O:15][CH3:16]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 588230083-(4-Hydroxy-3-methoxy-phenyl)-2-methoxy-propionic acid methyl ester

Product 1

HCID 18443662HCID 18443662, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 1N aqueous lithium hydroxide solution was added to a solution of 3-(4-hydroxy-3-methoxy-phenyl)-2-methoxy-propionic acid methyl ester (280 mg, 1.17 mmol) in THF at room temperature, and the reaction mixture stirred overnight. The aqueous phase was extracted with ethyl acetate (20 mL), acidified to pH 2, and extracted with ethyl acetate (3×15 mL). The later organic layers were combined and washed with water (15 mL) and brine (10 mL), dried (MgSO4), filtered, and concentrated under vacuum to produce 3-(4-hydroxy-3-methoxy-phenyl)-2-methoxy-propionic acid as an oil (183 mg, 74%). 1H-NMR (250.13 MHz, CDCl3): δ 6.83 (1H, d, J=7.8), 6.74 (1H, s), 6.72 (1H, d, J=7.8), 3.99 (1H dd, J=7.8, 4.0), 3.85 (s, 3H), 3.40 (s, 3H), 3.09 (1H, dd, J=14.2, 4.0), 2.91 (1H dd, J=14.2, 7.8).

Workup

  1. extractionThe aqueous phase was extracted with ethyl acetate (20 mL)
  2. extractionextracted with ethyl acetate (3×15 mL)
  3. washwashed with water (15 mL) and brine (10 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-2d4d67a8859f406389ddf0bfde39991c
Source dataset
uspto-grants-2007_03
Patent number
US07192982B2

Linked notes

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