Water → 4-(Naphthalen-1-yl)-4-oxobut-2-enoic acid

HRID 1387321Notes

Reaction equation

HRID 1387321 reaction equation
[C:1]([OH:8])(=O)/[CH:2]=[CH:3]\[C:4]([OH:6])=[O:5].Br[C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12][CH:11]=1.O>O1CCCC1>[C:18]1([C:1](=[O:8])[CH:2]=[CH:3][C:4]([OH:6])=[O:5])[C:19]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 962WaterHCID 70011-BromonaphthaleneHCID 444266Maleic Acid2×

Product 1

HCID 541869794-(Naphthalen-1-yl)-4-oxobut-2-enoic acidYield 30%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
78 °C

Procedure

5.88 g(60 mmol) of dry maleic acid was dissolved in 100 ml of dry tetrahydrofuran and the mixture was cooled down to 78° C. 4.14 g(20 mmol) of 1-bromonaphthalene was dissolved in 100 ml of dry tetrahydrofuran and 13.8 ml of 1.6N n-butyllithium-hexane solution was added thereto at 78° C. This reaction solution was stirred for 5 minutes and then it was added to the dry maleic acid solution prepared in advance using cannula. The resulting mixture was stirred for 10 minutes, and water was added thereto to stop the reaction. The solvent was removed under reduced pressure, and the residue was acidified by 1N aqueous hydrochloric acid solution and extracted with ethyl acetate. The organic layer was washed with water and aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, concentrated under reduced pressure and subjected to column chromatography(eluent: ethyl acetate/hexane=2/1, v/v) to give 1.35 g(6.0 mmol; Yield 30%) of the title compound.

Workup

  1. addition13.8 ml of 1.6N n-butyllithium-hexane solution was added
  2. customat 78° C
  3. customprepared in advance
  4. stirringThe resulting mixture was stirred for 10 minutes
  5. customthe reaction
  6. customThe solvent was removed under reduced pressure
  7. extractionextracted with ethyl acetate
  8. washThe organic layer was washed with water and aqueous sodium chloride solution
  9. dry with materialdried over anhydrous magnesium sulfate
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-15cf53cc052047f58999b5baade6fdde
Source dataset
uspto-grants-2001_07
Patent number
US06268363B1

Reaction notes

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