Water → 3-(3,5-Difluorophenyl)pentanedioic acid

HRID 362880Notes

Reaction equation

HRID 362880 reaction equation
[OH-:1].[Na+].[OH2:3].C([CH:7]1[CH:12]([C:13]2[CH:18]=[C:17]([F:19])[CH:16]=[C:15]([F:20])[CH:14]=2)[CH:11]([C:21](=[O:23])C)C(O)(C)C[C:8]1=[O:26])(=O)C>C(O)C>[F:19][C:17]1[CH:18]=[C:13]([CH:12]([CH2:7][C:8]([OH:26])=[O:3])[CH2:11][C:21]([OH:23])=[O:1])[CH:14]=[C:15]([F:20])[CH:16]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 15896146HCID 15896146, compound

Product 1

HCID 158961473-(3,5-Difluorophenyl)pentanedioic acidYield 33%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a hot (95° C.) solution prepared from sodium hydroxide (322 g, 8.1 mol) and deionized water (322 ml) was added a mixture of 2,4-diacetyl-3-(3,5-difluorophenyl)-5-hydroxy-5-methyl-1-cyclohexanone (43 g, 0. 112 mol) in ethanol (322 ml) with rapid stirring. The resulting mixture was refluxed for 4 hrs using an oil bath at 140° C. The ethanol was removed by spin evaporation in vacuo and the resulting slurry was cooled with an ice bath, and concentrated hydrochloric acid (12N) was added to adjust the pH to approximately 1. The precipitate was dissolved by the addition of water, and this aqueous solution was extracted with ethyl acetate (total volume 1500 ml). The ethyl acetate extracts were combined, washed with water, dried with MgSO4, and the volatiles were removed by spin evaporation in vacuo. Recrystallization of the residue from dichloromethane and hexanes gave 9.10 g (33%) of 3-(3,5-difluorophenyl)glutaric acid: m.p., 170°-172° C.;

Workup

  1. additionwas added
  2. temperatureThe resulting mixture was refluxed for 4 hrs
  3. customat 140° C
  4. customThe ethanol was removed by spin evaporation in vacuo
  5. temperaturethe resulting slurry was cooled with an ice bath
  6. additionconcentrated hydrochloric acid (12N) was added
  7. dissolutionThe precipitate was dissolved by the addition of water
  8. extractionthis aqueous solution was extracted with ethyl acetate (total volume 1500 ml)
  9. washwashed with water
  10. dry with materialdried with MgSO4
  11. customthe volatiles were removed by spin evaporation in vacuo
  12. customRecrystallization of the residue from dichloromethane and hexanes

Sources & evidence

ORD record
ord-4a5025f1efa14d959c6454e3fc631487
Source dataset
uspto-grants-1999_02
Patent number
US05872118

Reaction notes

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