Methanol → HCID 131727892, compound

HRID 1879430Notes

Reaction equation

HRID 1879430 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH:8]([CH3:12])[C:9]([OH:11])=[O:10])[CH:5]=[CH:4][C:3]=1[C:13]1[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=1.S(=O)(=O)(O)O.[CH3:28]O>>[F:1][C:2]1[C:3]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:20])([F:21])[F:22])=[CH:15][CH:14]=2)=[CH:4][CH:5]=[C:6]([CH:8]([CH3:12])[C:9]([O:11][CH3:28])=[O:10])[CH:7]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 99727752-Fluoro-α-methyl-4′-(trifluoromethyl)[1,1′-biphenyl]-4-acetic acid

Product 1

HCID 131727892HCID 131727892, compoundYield 95%

Procedure

A solution of 2-(2-fluoro-4′-trifluoromethylbiphenyl-4-yl)propionic acid (0.2 g, 0.64 mmoles) in methanol (3 ml) is added with 98% sulfuric acid (0.5 g) and refluxed for 2.5 hours. The solvent is removed under vacuum, the residue is taken up with ethyl acetate (5 ml) and washed with a 5% NaHCO3 solution (5 ml), then with water. The solution is dried over Na2SO4 and concentrated under vacuum to afford an oil (0.2 g, 95%).

Workup

  1. temperaturerefluxed for 2.5 hours
  2. customThe solvent is removed under vacuum
  3. washwashed with a 5% NaHCO3 solution (5 ml)
  4. dry with materialThe solution is dried over Na2SO4
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-b76ef07dc68448f0b0dcc3047e3e5fec
Source dataset
uspto-grants-2012_11
Patent number
US08314268B2

Reaction notes

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