4-Fluorobenzoic Acid → 4-Fluorobenzoic Acid

HRID 247185Notes

Reaction equation

HRID 247185 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1>C1(OC2C=CC=CC=2)C=CC=CC=1.O=O>[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][C:4]2[CH:5]=[CH:9][CH:10]=[C:2]([F:1])[CH:3]=2)=[O:7])=[CH:4][CH:3]=1.[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 1

HCID 99734-Fluorobenzoic Acid

Product 2

HCID 99734-Fluorobenzoic AcidHCID 141493914-Fluorobenzoic acid, 3-fluorophenyl ester

Reagents, catalysts & solvents 2

HCID 977OxygenSolvent2×HCID 7583Diphenyl EtherSolvent

Conditions

Temperature
240 °C

Procedure

A 25-ml 2-necked Kjeldahl flask fitted with an air-cooling line and an oxygen introducing line was charged with 2.1 g of p-fluorobenzoic acid, 1.99 g of cupric oxide, and 2 ml of diphenyl ether as solvent, after which it was heated at 240° C. over an oil bath while blowing in oxygen at a rate of 30 ml per minute for 90 minutes. After cooling, the experiment was carried out as in Example 1 to recover 0.121 g of p-fluorobenzoic acid from the filtration residue. And from the filtrate there were obtained 0.656 g of m-fluorophenyl p-flurobenzoate and 1.000 g of p-fluorobenzoic acid by column chromatography. The yield of m-fluorophenyl p-fluorobenzoate was 37.4%, and the selectivity was 80.3%.

Workup

  1. customA 25-ml 2-necked Kjeldahl flask fitted with an air-cooling line
  2. temperatureAfter cooling
  3. filtrationto recover 0.121 g of p-fluorobenzoic acid from the filtration residue

Sources & evidence

ORD record
ord-5838d2e0747b4e2891ee5d6cf7a37a72
Source dataset
uspto-grants-1987_11
Patent number
US04705884

Reaction notes

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