2-(4-Chloro-benzylidene)-3-methyl-succinic acid → 6-Chloro-4-hydroxy-3-methyl-naphthalene-2-carboxylic acid

HRID 238609

Reaction equation

HRID 238609 reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([CH:6]=[C:7]([CH:11]([CH3:15])[C:12]([OH:14])=O)[C:8]([OH:10])=[O:9])=[CH:4][CH:3]=1>FC(F)(F)S(O)(=O)=O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:16][CH:17]=1)[CH:6]=[C:7]([C:8]([OH:10])=[O:9])[C:11]([CH3:15])=[C:12]2[OH:14]

Participants

3

Reactant 1

HCID 673042002-(4-Chloro-benzylidene)-3-methyl-succinic acid

Product 1

HCID 593265616-Chloro-4-hydroxy-3-methyl-naphthalene-2-carboxylic acidYield 97.6%

Reagents, catalysts & solvents 1

HCID 62406Trifluoromethanesulfonic acidSolvent

Procedure

To a flask containing trifluoromethanesulfonic acid (40 mL), 2-(4-chloro-benzylidene)-3-methyl-succinic acid (14.0 g) was added in portions. After being stirred at room temperature for 18 hours, the resulting mixture was poured onto ice-water, and stirred for 15 minutes. The formed precipitate was collected by filtration, and dissolved in ethyl acetate (150 mL). The solution was dried over sodium sulfate, and concentrated in vacuo. The residue was precipitated from ethyl acetate/petroleum ether (1:10) to afford 6-chloro-4-hydroxy-3-methyl-naphthalene-2-carboxylic acid (12.7 g, 97.6%) as a pink solid.

Workup

  1. additionwas added in portions
  2. additionthe resulting mixture was poured onto ice-water
  3. stirringstirred for 15 minutes
  4. filtrationThe formed precipitate was collected by filtration
  5. dissolutiondissolved in ethyl acetate (150 mL)
  6. dry with materialThe solution was dried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue was precipitated from ethyl acetate/petroleum ether (1:10)

Sources & evidence

ORD record
ord-4daf9ad9e7f3421abab489580f9c0134
Source dataset
uspto-grants-2014_02
Patent number
US08642629B2

Linked notes

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