Formic Acid → 2,2-Bis(4-fluorophenyl)acetic acid

HRID 1167250Notes

Reaction equation

HRID 1167250 reaction equation
[F:1][C:2]1[CH:16]=[CH:15][C:5]([CH:6](O)[C:7]2[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.OS(O)(=O)=O.[CH:22]([OH:24])=[O:23].[C]=O>O>[F:1][C:2]1[CH:16]=[CH:15][C:5]([CH:6]([C:7]2[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=2)[C:22]([OH:24])=[O:23])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 284Formic AcidHCID 1118Sulfuric AcidHCID 1230494,4'-Difluorobenzhydryl alcoholHCID 178418416HCID 178418416, compound

Product 1

HCID 135116842,2-Bis(4-fluorophenyl)acetic acidYield 103.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 4,4′-difluorobenzhydrol (10.0 g, 45.4 mmol, 1 equiv) in H2SO4 (37 M; 200 mL, 7.4 mol, 160 equiv) in an ice bath was added formic acid (20 mL, 24 g, 0.53 mol, 12 equiv) with no stirring. After a few seconds, carbon monoxide evolution was observed. The reaction was allowed to stand without stirring for 3.5 h. The reaction mixture was carefully poured into H2O (1000 mL) (highly exothermic). The aqueous mixture was extracted with EtOAc (1×250 mL). The organic layer was dried (anh. Na2SO4) and rotary evaporated (75° C.) to yield 11.7 g of an orange oil. This oil was dissolved in Et2O (100 mL) and extracted with 2 M NaOH (1×50 mL). The aqueous layer was then acidified with 12 M HCl (8 mL) and extracted with EtOAc (1×50 mL). The organic layer was dried (anh. Na2SO4), rotary evaporated (75° C.), and put under high vacuum for 16 h. This provided 6.15 g (54.6%) of product as a yellow, crystalline solid.

Workup

  1. waitAfter a few seconds
  2. extractionThe aqueous mixture was extracted with EtOAc (1×250 mL)
  3. dry with materialThe organic layer was dried (anh. Na2SO4)
  4. customrotary evaporated (75° C.)

Sources & evidence

ORD record
ord-3041b09c74fc4770aa8bbfcaf1a6ffa5
Source dataset
uspto-grants-2003_09
Patent number
US06617358B1

Reaction notes

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