Sodium Hydroxide → 3-(3-Methoxy-benzyloxy)-phthalic acid

HRID 1915157Notes

Reaction equation

HRID 1915157 reaction equation
C[O:2][C:3](=[O:24])[C:4]1[C:5](=[C:10]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH3:23])[CH:17]=2)[CH:11]=[CH:12][CH:13]=1)[C:6]([O:8]C)=[O:7].[OH-].[Na+]>>[CH3:23][O:22][C:18]1[CH:17]=[C:16]([CH:21]=[CH:20][CH:19]=1)[CH2:15][O:14][C:10]1[CH:11]=[CH:12][CH:13]=[C:4]([C:3]([OH:24])=[O:2])[C:5]=1[C:6]([OH:8])=[O:7]

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 669065723-(3-Methoxy-benzyloxy)-phthalic acid dimethyl ester

Product 1

HCID 669063963-(3-Methoxy-benzyloxy)-phthalic acid

Procedure

A solution of 3-(3-methoxy-benzyloxy)-phthalic acid dimethyl ester (2.0 g crude, 5.5 mmol) in reagent alcohol (100 mL) and 3 N sodium hydroxide (35 mL) was refluxed for two hours. The solution was evaporated and the residue was dissolved in water (80 mL) and washed with methylene chloride (3×70 mL) then acidified to pH around 4. The resulting mixture was extracted with ethyl acetate (2×60 mL) and the combined organic layers was washed with water (2×70 mL), dried and concentrated to give 3-(3-methoxy-benzyloxy)-phthalic acid as an off-white solid (1.6 g, 98% crude yield). The product was used in the next step without further purification.

Workup

  1. customThe solution was evaporated
  2. dissolutionthe residue was dissolved in water (80 mL)
  3. washwashed with methylene chloride (3×70 mL)
  4. extractionThe resulting mixture was extracted with ethyl acetate (2×60 mL)
  5. washthe combined organic layers was washed with water (2×70 mL)
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-fc9d7e4505a0474db0193c0654672c72
Source dataset
uspto-grants-2013_12
Patent number
US08614328B2

Reaction notes

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