HCID 66906613, compound → HCID 66906781, compound

HRID 1690441Notes

Reaction equation

HRID 1690441 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]([F:22])[CH:17]=2)[CH:11]=[CH:12][CH:13]=1)[C:6]([O:8]C)=[O:7]>[OH-].[Na+]>[F: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 66906613HCID 66906613, compound

Product 1

HCID 66906781HCID 66906781, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A solution of 3-(3-fluoro-benzyloxy)-phthalic acid dimethyl ester (2.4 g crude, 6.7 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 organic layers was washed with water (2×100 mL), dried and concentrated to give 3-(3-fluoro-benzyloxy)-phthalic acid as an off-white solid (1.9 g, 101% 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 organic layers was washed with water (2×100 mL)
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-cc5763ba5e2d4238801897ab43861a75
Source dataset
uspto-grants-2012_04
Patent number
US08153659B2

Reaction notes

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