Hydrochloric Acid → Benzoic acid, 2-(2-furanylcarbonyl)-

HRID 2211108Notes

Reaction equation

HRID 2211108 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[CH:2]1.C([Li])CCC.[Li].[C:12]1(=[O:22])[O:17][C:15](=[O:16])[C:14]2=[CH:18][CH:19]=[CH:20][CH:21]=[C:13]12.Cl>O1CCCC1>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:12]([C:13]1[CH:21]=[CH:20][CH:19]=[CH:18][C:14]=1[C:15]([OH:17])=[O:16])=[O:22]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 6811Phthalic AnhydrideHCID 8029FuranHCID 3028194LithiumHCID 178418339Butyllithium

Product 1

HCID 358265Benzoic acid, 2-(2-furanylcarbonyl)-Yield 18.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

3.4 g of furan was dissolved in 30 ml of tetrahydrofuran, and the solution was added dropwise to 34 ml of normal butyllithium (1.6M, hexane solution) at -40° C. After stirring the resultant solution at 0° C. for 4 hours, the lithium reagent was added dropwise to a solution of 7.4 g of phthalic anhydride in 100 ml of tetrahydrofuran at -70° C. After stirring the solution at the same temperature for 1 hour, the reaction solution was poured into 0.5-N hydrochloric acid, and extracted with chloroform. By purification by column chromatography (eluent: chloroform, methanol), 2.0 g of o-(2-furoyl) benzoic acid was obtained.

Workup

  1. extractionextracted with chloroform
  2. customBy purification by column chromatography (eluent: chloroform, methanol)

Sources & evidence

ORD record
ord-8a6623b7eee04bee97278e3cb290863e
Source dataset
uspto-grants-1995_10
Patent number
US05462941

Reaction notes

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