4-Hydroxybenzoic Acid → HCID 18435337, compound

HRID 2304370Notes

Reaction equation

[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.C[O-].[Na+].F[C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[C:17]([CH3:24])[CH:16]=1.Cl>CO.O>[CH3:24][C:17]1[CH:16]=[C:15]([CH:20]=[CH:19][C:18]=1[N+:21]([O-:23])=[O:22])[O:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 125 °C

Procedure

4-hydroxybenzoic acid (13.8 g, 0.1 mole) was dissolved in methanol and to this solution was added, sodium methoxide (10.8 g, 0.2 mole). The solution was then evaporated to dryness. To the resulting solid was added DMF (500 mL) followed by 4-fluoro-2-methyl-1-nitrobenzene (available from Aldrich under 5-fluoro-2-nitro-toluene) (10.2 mL 0.1 mole). The mixture was heated at 125° C. for 2 hours, cooled and poured into 3 L of water, acidified to pH2 with 2M HCl and extracted twice with ethyl acetate. The combined organic layers were washed with water, dried and evaporated to dryness. The resulting solid was triturated with ether to give 4-(3-methyl-4-nitro-phenoxy)-benzoic acid (compound 1) as a white solid 6.1 g (22% yield; melting point=187-190° C.).

Workup

additionwas added
customThe solution was then evaporated to dryness
additionTo the resulting solid was added DMF (500 mL)
temperaturecooled
extractionextracted twice with ethyl acetate
washThe combined organic layers were washed with water
customdried
customevaporated to dryness
customThe resulting solid was triturated with ether

Sources & evidence

ORD record: ord-fc32525ea67f402ea8b129cb5217af4d
Source dataset: uspto-grants-2002_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06436691B1

Reaction notes

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