4-(4-Fluoro-benzyloxy)-phthalic acid bis-(4-fluoro-benzyl) ester → 4-(4-Fluoro-benzyloxy)-phthalic acid

HRID 1070679Notes

Reaction equation

HRID 1070679 reaction equation
FC1C=CC(C[O:7][C:8](=[O:35])[C:9]2[C:10](=[CH:22][C:23]([O:26][CH2:27][C:28]3[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=3)=[CH:24][CH:25]=2)[C:11]([O:13]CC2C=CC(F)=CC=2)=[O:12])=CC=1>O1CCCC1.O>[F:34][C:31]1[CH:30]=[CH:29][C:28]([CH2:27][O:26][C:23]2[CH:22]=[C:10]([C:11]([OH:13])=[O:12])[C:9](=[CH:25][CH:24]=2)[C:8]([OH:35])=[O:7])=[CH:33][CH:32]=1

Participants

4

Reactant 1

HCID 697368654-(4-Fluoro-benzyloxy)-phthalic acid bis-(4-fluoro-benzyl) ester

Product 1

HCID 223970954-(4-Fluoro-benzyloxy)-phthalic acidYield 56%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-(4-fluoro-benzyloxy)-phthalic acid bis-(4-fluoro-benzyl) ester (7.8 g, 15.4 mmol) lithium hydroxide monohydrate (1.8 g, 46.2 mmol) in tetrahydrofuran (60 mL) and water (60 mL) was stirred at room temperature for 72 h. The mixture was then evaporated followed by acidification to pH 2 at 0° C. with concentrated HCl. The organic layer was then diluted with ethyl acetate, separared, washed with water and dried over sodium sulfate. Filtration and half evaporation gave a white suspension which was filtered off and washed with ether to afford the title compound (2.5 g, 56%) as a white solid.

Workup

  1. customThe mixture was then evaporated
  2. customfollowed by acidification to pH 2 at 0° C. with concentrated HCl
  3. additionThe organic layer was then diluted with ethyl acetate
  4. washwashed with water
  5. dry with materialdried over sodium sulfate
  6. filtrationFiltration and half evaporation
  7. customgave a white suspension which
  8. filtrationwas filtered off
  9. washwashed with ether

Sources & evidence

ORD record
ord-bd24580e823649e9b37825c97ec4df82
Source dataset
uspto-grants-2005_06
Patent number
US06903095B2

Reaction notes

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