Hydrochloric Acid → 2-(4-Fluorophenoxy)benzoic acid

HRID 1904308Notes

Reaction equation

I[C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].C(=O)([O-])[O-].[K+].[K+].[N+](C1C=CC=CC=1)([O-])=O.[F:26][C:27]1[CH:32]=[CH:31][C:30]([OH:33])=[CH:29][CH:28]=1.Cl>O.[Cu].C(Cl)(Cl)Cl>[F:26][C:27]1[CH:32]=[CH:31][C:30]([O:33][C:2]2[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=2[C:4]([OH:6])=[O:5])=[CH:29][CH:28]=1

Participants

Conditions

Temperature: 160 °C

Procedure

To 147 g of iodobenzoic acid and 45.5 g of potassium carbonate are added 57 ml of nitrobenzene. The mixture is heated with stirring at 160° C. for 40 minutes. To the heated mixture is added an additional 46.5 g of potassium carbonate and then successively 73.1 g of 4-fluorophenol, another 46.5 g of potassium carbonate and 0.3 g of copper powder. After these additions, the mixture is stirred at 160° C. for 45 minutes and the resulting solid is cooled to 0° C. The cooled solid is mixed with 100 ml of water and 220 ml of 6N hydrochloric acid. The acidic mixture is diluted with water to a volume of one liter and then mixed with 450 ml of chloroform. The white solid is filtered off and washed with chloroform and water. The solid is dissolved in hot acetone, cooled and filered to leave a white crystalline product, mp 146°-147° C. of 2-(4-fluorophenoxy)benzoic acid.

Workup

temperatureThe mixture is heated
stirringAfter these additions, the mixture is stirred at 160° C. for 45 minutes
temperaturethe resulting solid is cooled to 0° C
filtrationThe white solid is filtered off
washwashed with chloroform and water
dissolutionThe solid is dissolved in hot acetone
temperaturecooled

Sources & evidence

ORD record: ord-66d8f3f8669049edbb8e6523c40de46a
Source dataset: uspto-grants-1989_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04837227

Reaction notes

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