HCID 66906613, compound → HCID 66906781, compound

HRID 1915146Notes

Reaction equation

HRID 1915146 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-70c5c02cf5ef4901a1fcc713e644aa01
Source dataset
uspto-grants-2013_12
Patent number
US08614328B2

Reaction notes

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