Lithium hydroxide, monohydrate → 4-(4-Chlorophenyl)-4-(methoxyimino)butanoic acid
Reaction equation
O.[OH-].[Li+].[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([C:11](=[N:19][O:20][CH3:21])[CH2:12][CH2:13][C:14]([O:16]CC)=[O:15])=[CH:7][CH:6]=1>O.C1COCC1.C(O)C.CCOC(C)=O>[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([C:11](=[N:19][O:20][CH3:21])[CH2:12][CH2:13][C:14]([OH:16])=[O:15])=[CH:7][CH:6]=1Participants
7
Reactant 2
Product 1
Reagents, catalysts & solvents 4
Conditions
- Temperature
- 20 °C
Procedure
Lithium hydroxide monohydrate (9.59 g, 228.57 mmol) was added to ethyl 4-(4-chlorophenyl)-4-(methoxyimino)butanoate (Intermediate 52) (12.33 g, 45.71 mmol) in water (25.4 mL), THF (102 mL) and ethanol (102 mL). The resulting solution was stirred at 20° C. for 1 day. The reaction mixture was diluted with EtOAc (200 mL) and washed with water (200 mL). The aqueous was adjusted to pH5 with 1M citric acid solution then extracted with EtOAc (3×150 mL). The organic extracts were washed with saturated brine (25 mL) then dried over MgSO4, filtered and evaporated to afford desired product 4-(4-chlorophenyl)-4-(methoxyimino)butanoic acid (7.63 g, 69.1%) as a light yellow solid.
Workup
- washwashed with water (200 mL)
- extractionthen extracted with EtOAc (3×150 mL)
- washThe organic extracts were washed with saturated brine (25 mL)
- dry with materialthen dried over MgSO4
- filtrationfiltered
- customevaporated
Sources & evidence
- ORD record
- ord-c558eee4cfbc47ab816ab9469084dc81
- Source dataset
- uspto-grants-2012_01
- Patent number
- US08101623B2
Reaction notes
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