Sodium Hydroxide → 4-(4'-Methoxy-biphenyl-4-yl)-4-oxo-butyric acid

HRID 381839

반응식

HRID 381839 반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([C:15](=[O:22])[CH2:16][CH2:17][C:18]([O:20]C)=[O:19])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.[OH-].[Na+]>CO>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:14]=[CH:13][C:12]([C:15](=[O:22])[CH2:16][CH2:17][C:18]([OH:20])=[O:19])=[CH:11][CH:10]=2)=[CH:7][CH:8]=1

참가 물질

4

반응물 2

HCID 14798Sodium Hydroxide2회HCID 5273114-(4'-Methoxy-biphenyl-4-yl)4-oxo-butyric acid, methyl ester

생성물 1

HCID 230052384-(4'-Methoxy-biphenyl-4-yl)-4-oxo-butyric acid수율 72.6%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a stirred suspension of 4-(4′-methoxy-biphenyl-4-yl)-4-oxo-butyric acid, methyl ester (1.342 g, 0.00450 mol) in methanol (15 mL) at room temperature was added 50/50 wt/wt aqueous sodium hydroxide (0.41 g, 0.0051 mol), and the mixture was stirred for 3 days, for convenience. To the mixture was added 1.0 M aqueous sodium hydroxide (0.45 mL, 0.00045 mol) and stirring was continued for 1 day. The mixture was rotary evaporated, and the residue was partitioned between dichloromethane-tetrahydrofuran (50/50 v/v) and 0.2 M aqueous hydrochloric acid. The organic layer was washed with brine and dried (Na2SO4). The mixture was rotary evaporated, and the residue was purified by chromatography on silica gel (154 g, 230-400 mesh), eluting with dichloromethane (7×225 mL); dichloromethane-methanol (19:1, 7×225 mL) to give 0.929 g of 4-(4′-methoxy-biphenyl-4-yl)-4-oxo-butyric acid as an off-white solid; mp 197-199° C.

후처리

  1. stirringstirring
  2. waitwas continued for 1 day
  3. customthe residue was partitioned between dichloromethane-tetrahydrofuran (50/50 v/v) and 0.2 M aqueous hydrochloric acid
  4. washThe organic layer was washed with brine
  5. dry with materialdried (Na2SO4)
  6. customthe residue was purified by chromatography on silica gel (154 g, 230-400 mesh)
  7. washeluting with dichloromethane (7×225 mL)

출처 및 근거

ORD 기록
ord-f197e56dda1a498282eeb23e99403a77
출처 데이터셋
uspto-grants-2001_10
특허 번호
US06307089B2

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