Lithium Hydroxide → 3-Methyl-4-(1-piperidinyl)benzoic acid

HRID 1950825노트

반응식

HRID 1950825 반응식
[OH-].[Li+].[CH3:3][C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][C:13]=1[N:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)[C:7]([O:9]C)=[O:8]>C1COCC1.O>[CH3:3][C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][C:13]=1[N:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)[C:7]([OH:9])=[O:8]

참가 물질

5

반응물 2

HCID 3939Lithium HydroxideHCID 67529104HCID 67529104, 화합물

생성물 1

HCID 337808373-Methyl-4-(1-piperidinyl)benzoic acid수율 89%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
50 °C

실험 절차

Lithium hydroxide (2.5 g; 103 mmol; 5 eq.) was added to a solution of methyl 3-methyl-4-piperidin-1-ylbenzoate (4.8 g; 20.6 mmol; 1 eq.) in THF (100 mL) and water (5 mL) and the reaction mixture was stirred at 50° C. for 12 hours. The solvent was removed in vacuo, the residue diluted with water and the aqueous layer washed with DCM (2×50 mL). The aqueous layer was acidified to pH 4 with conc. HCl and extracted with ethyl acetate (2×100 mL). The combined organic layer was washed with brine, dried over sodium sulfate and concentrated in vacuo to afford the title compound (4.0 g, 89%) as a yellow solid.

후처리

  1. customThe solvent was removed in vacuo
  2. additionthe residue diluted with water
  3. washthe aqueous layer washed with DCM (2×50 mL)
  4. extractionextracted with ethyl acetate (2×100 mL)
  5. washThe combined organic layer was washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-f9e7a39ec4804e46ba8a6328980040d5
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08404676B2

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