Sodium Hydroxide → HCID 66906835, compound

HRID 709588Notes

Reaction equation

HRID 709588 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][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)[CH:11]=[CH:12][CH:13]=1)[C:6]([O:8]C)=[O:7].[OH-].[Na+]>>[CH3:23][O:22][C:19]1[CH:18]=[CH:17][C:16]([CH2:15][O:14][C:10]2[CH:11]=[CH:12][CH:13]=[C:4]([C:3]([OH:24])=[O:2])[C:5]=2[C:6]([OH:8])=[O:7])=[CH:21][CH:20]=1

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 66906525HCID 66906525, compound

Product 1

HCID 66906835HCID 66906835, compound

Procedure

A stirred solution of 3-(4-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 in vacuo, and the residue was dissolved in water (80 mL) and washed with methylene chloride (3×70 mL), then acidified to pH around 4 by HCl. 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 in vacuo to give 3-(4-methoxy-benzyloxy)-phthalic acid as an off-white solid (1.6 g, 100% crude yield). The product was used in the next step without further purification.

Workup

  1. customThe solution was evaporated in vacuo
  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 in vacuo

Sources & evidence

ORD record
ord-165d1902bda34b5e994c9c7e7471da8e
Source dataset
uspto-grants-2015_11
Patent number
US09181216B2

Reaction notes

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