HCID 66906596, compound → HCID 66906359, compound

HRID 1690444Notes

Reaction equation

HRID 1690444 reaction equation
C[O:2][C:3](=[O:23])[C:4]1[C:5](=[C:10]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([Br:22])[CH:17]=2)[CH:11]=[CH:12][CH:13]=1)[C:6]([O:8]C)=[O:7]>[OH-].[Na+]>[Br: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:23])=[O:2])[C:5]=1[C:6]([OH:8])=[O:7]

Participants

3

Reactant 1

HCID 66906596HCID 66906596, compound

Product 1

HCID 66906359HCID 66906359, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A solution of 3-(3-bromo-benzyloxy)-phthalic acid dimethyl ester (1.9 g, 5.8 mmol) in reagent alcohol (100 mL) and 3 N sodium hydroxide (60 mL) was refluxed for two hours. The solution was evaporated and the residue was dissolved in water (100 mL) and washed with methylene chloride (3×100 mL) then acidified to pH around 4. The resulting mixture was extracted with ethyl acetate (2×100 mL) and the combined extracts was washed with water (2×100 mL), dried and concentrated to give 3-(3-bromo-benzyloxy)-phthalic acid as an off-white solid (2.5 g, 109% 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 (100 mL)
  3. washwashed with methylene chloride (3×100 mL)
  4. extractionThe resulting mixture was extracted with ethyl acetate (2×100 mL)
  5. washthe combined extracts was washed with water (2×100 mL)
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-e85543d301064b21ac464580c9c21c39
Source dataset
uspto-grants-2012_04
Patent number
US08153659B2

Reaction notes

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