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

HRID 1979158

Reaction equation

HRID 1979158 reaction equation
[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

Participants

4

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 5273114-(4'-Methoxy-biphenyl-4-yl)4-oxo-butyric acid, methyl ester

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-3b0361d19c994d429e5f3955e33ef7c5
Source dataset
uspto-grants-2001_05
Patent number
US06239288B1

Linked notes

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