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

HRID 238609

반응식

HRID 238609 반응식
[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]

참가 물질

3

반응물 1

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

생성물 1

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

시약·촉매·용매 1

HCID 62406Trifluoromethanesulfonic acid용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-4daf9ad9e7f3421abab489580f9c0134
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08642629B2

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