Ethanol → Ethyl 2',4'-Difluoro-4-hydroxy[1,1'-biphenyl]-3-carboxylate

HRID 85396

Reaction equation

HRID 85396 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[C:11]([C:16]([OH:18])=[O:17])[CH:10]=1.[CH2:19](O)[CH3:20]>S(=O)(=O)(O)O>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[C:11]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:10]=1

Participants

4

Reactant 2

HCID 702EthanolHCID 3059Diflunisal

Product 1

HCID 23078331Ethyl 2',4'-Difluoro-4-hydroxy[1,1'-biphenyl]-3-carboxylate

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
80 °C

Procedure

2′,4′-difluoro-4-hydroxybiphenyl-3-carboxylic acid (1.0 g, 4.0 mmol) was dissolved in ethanol (30 mL) and sulfuric acid (8 mL). The solution was stirred (80° C., 18 h) and then concentrated under reduced pressure. The residue was dissolved in ethyl acetate and washed with water, brine and dried over MgSO4. Solvent evaporation afforded ethyl 2′,4′-difluoro-4-hydroxybiphenyl-3-carboxylate (1.0 g). Mass calculated for C15H12F2O3=278.25; found: [M+H]+=279.1.

Workup

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed with water, brine
  4. dry with materialdried over MgSO4
  5. customSolvent evaporation

Sources & evidence

ORD record
ord-a286ace1d6794b16b595376991b025a4
Source dataset
uspto-grants-2014_09
Patent number
US08846972B2

Linked notes

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