Sodium Hydroxide → HCID 21927967, compound

HRID 1954914Notes

Reaction equation

HRID 1954914 reaction equation
[OH-].[Na+].[C:3]([CH:8]([CH:14]([C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[CH:22]=1)[CH2:15][C:16]([O:18]CC)=[O:17])C(OCC)=O)([O:5]CC)=[O:4]>O.C(O)C>[F:27][C:23]1[CH:22]=[C:21]([CH:14]([CH2:8][C:3]([OH:5])=[O:4])[CH2:15][C:16]([OH:18])=[O:17])[CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 23293688HCID 23293688, compound

Product 1

HCID 21927967HCID 21927967, compoundYield 77.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a hot solution of sodium hydroxide (19.15 g, 0.479 mol) in water (50 mL) was added a solution of diethyl 2-carbethoxy-3-(3-fluorophenyl)glutarate (18.8 g, 0.0532 mol) in ethanol (36 ml). The resulting slurry was refluxed for 5 hrs. The mixture was poured into icewater and the ethanol was removed by spin evaporation in vacuo. The residual aqueous solution was acidified with concentrated hydrochloric acid (12 N) and the solution (200 mL) was extracted with ethyl acetate (3×300 ml). The ethyl acetate layers were combined, washed with water (50 ml) and the volatiles were removed by spin evaporation in vacuo to give a solid that was recrystallized from dichloromethane and hexanes to give 9.3 g (77%) of 3-(3-fluorophenyl)glutaric acid a white solid; m.p., 126-127.5° C.;

Workup

  1. temperatureThe resulting slurry was refluxed for 5 hrs
  2. additionThe mixture was poured into icewater
  3. customthe ethanol was removed by spin evaporation in vacuo
  4. extractionthe solution (200 mL) was extracted with ethyl acetate (3×300 ml)
  5. washwashed with water (50 ml)
  6. customthe volatiles were removed by spin evaporation in vacuo
  7. customto give a solid
  8. customthat was recrystallized from dichloromethane and hexanes

Sources & evidence

ORD record
ord-5657811b34774ceca4254c9942b30b6f
Source dataset
uspto-grants-2000_09
Patent number
US06124284

Reaction notes

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