Sodium Hydroxide → HCID 66906396, compound

HRID 709564Notes

Reaction equation

HRID 709564 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 66906396HCID 66906396, compound

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-d61de74a51784536a89024f1bc5513cd
Source dataset
uspto-grants-2015_11
Patent number
US09181216B2

Reaction notes

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