Acetone → 3'-(Trifluoromethoxy)[1,1'-biphenyl]-4-carboxylic acid

HRID 1470610Notes

Reaction equation

HRID 1470610 reaction equation
[F:1][C:2]([F:19])([F:18])[O:3][C:4]1[CH:5]=[C:6]([C:10]2[CH:15]=[CH:14][C:13]([CH:16]=[O:17])=[CH:12][CH:11]=2)[CH:7]=[CH:8][CH:9]=1.CC(C)=[O:22]>>[F:1][C:2]([F:18])([F:19])[O:3][C:4]1[CH:5]=[C:6]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([OH:22])=[O:17])=[CH:12][CH:11]=2)[CH:7]=[CH:8][CH:9]=1

Participants

3

Reactant 2

HCID 180AcetoneHCID 534038293'-(Trifluoromethoxy)[1,1'-biphenyl]-4-carbaldehyde

Product 1

HCID 532114543'-(Trifluoromethoxy)[1,1'-biphenyl]-4-carboxylic acidYield 82%

Procedure

To a cold solution of 3′-trifluoromethoxy-biphenyl-4-carbaldehyde (0.8 g, 3.0 mmol) in acetone (10 mL) the Jone's reagent was added slowly at 0° C. until reaction completes. Acetone was removed completely and diluted with water. The mixture was extracted with ethyl acetate and the combined organic layers were washed with water and brine, dried over sodium sulphate and concentrated to obtain the title compound (0.7 g, 82%).

Workup

  1. customAcetone was removed completely
  2. additiondiluted with water
  3. extractionThe mixture was extracted with ethyl acetate
  4. washthe combined organic layers were washed with water and brine
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b0f4c62cdeb644b89c956707bce40947
Source dataset
uspto-grants-2015_04
Patent number
US09006454B2

Reaction notes

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