Lithium hydroxide, monohydrate → 4-(2,4-Dichlorophenoxy)butyric acid

HRID 1690235노트

반응식

HRID 1690235 반응식
[Cl:1][C:2]1[CH:16]=[C:15]([Cl:17])[CH:14]=[CH:13][C:3]=1[O:4][CH2:5][CH2:6][CH2:7][C:8]([O:10]CC)=[O:9].O[Li].O>C1COCC1.O>[Cl:1][C:2]1[CH:16]=[C:15]([Cl:17])[CH:14]=[CH:13][C:3]=1[O:4][CH2:5][CH2:6][CH2:7][C:8]([OH:10])=[O:9]

참가 물질

5

반응물 2

HCID 168937Lithium hydroxide, monohydrateHCID 12375252Ethyl 4-(2,4-dichloro-phenoxy)butanoate

생성물 1

HCID 14894-(2,4-Dichlorophenoxy)butyric acid수율 74.3%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of ethyl 4-(2,4-dichlorophenoxy)-butyrate (57 g, crude from last step, about 0.2 mol) in THF (500 mL) and water (500 mL) was added LiOH.H2O (12.6 g, 0.3 mol), and the reaction mixture was stirred for 5 h at RT. The mixture was washed with Et2O (3×200 mL), and the aqueous layer was acidified by addition of HCl (20%) to pH˜2. The mixture was extracted with EtOAc (3×400 mL), the combined organic extracts were washed with water and brine, dried over Na2SO4 and concentrated in vacuo to give the butyric acid (37 g, 74.3% from 2,4-dichlorophenol) as a white solid. 1H-NMR (CDCl3): δ 7.36 (d, 1H, J=8.8 Hz), 7.18 (dd, 1H, J1=8.8 Hz, J2=2.4 Hz), 6.84 (d, 1H, J=8.8 Hz), 4.07 t, 2H, J=7.2 Hz), 2.64 (t, 2H, J=7.2 Hz), 2.17 (p, 2H, J=6.4 Hz).

후처리

  1. washThe mixture was washed with Et2O (3×200 mL)
  2. additionthe aqueous layer was acidified by addition of HCl (20%) to pH˜2
  3. extractionThe mixture was extracted with EtOAc (3×400 mL)
  4. washthe combined organic extracts were washed with water and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-162ce2a2560143448b9174d591d924cd
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08153655B2

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