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

HRID 431577Notes

Reaction equation

HRID 431577 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. MS: m/e=289.0 (M−H+).

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-e2b6ea3bd7334372a2b1a9d9980a4c7d
Source dataset
uspto-grants-2003_12
Patent number
US06660736B2

Reaction notes

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