Hydrochloric Acid → 4-(4-Chlorophenyl)-4-(methoxyimino)butanoic acid

HRID 423034Notes

Reaction equation

HRID 423034 reaction equation
[OH-].[Li+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10](=[N:18][O:19][CH3:20])[CH2:11][CH2:12][C:13]([O:15]CC)=[O:14])=[CH:6][CH:5]=1.Cl>C1COCC1.O>[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10](=[N:18][O:19][CH3:20])[CH2:11][CH2:12][C:13]([OH:15])=[O:14])=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 86632052Ethyl 4-(4-chlorophenyl)-4-(methoxyimino)butanoate2×

Product 1

HCID 866320534-(4-Chlorophenyl)-4-(methoxyimino)butanoic acidYield 95.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide (0.632 g, 26.40 mmol) was added in one portion at 20° C. to a solution of ethyl 4-(4-chlorophenyl)-4-(methoxyimino)butanoate (Intermediate 14) (1.78 g, 6.60 mmol) in THF (30 ml) and water (20 ml). The resulting solution was stirred at room temperature for 6 hours then acidified with dilute HCl and extracted with TBME (2×). The combined extracts were washed with brine, dried over MgSO4 and evaporated to give 4-(4-chlorophenyl)-4-(methoxyimino)butanoic acid (1.520 g, 95%) as a colourless solid.

Workup

  1. extractionextracted with TBME (2×)
  2. washThe combined extracts were washed with brine
  3. dry with materialdried over MgSO4
  4. customevaporated

Sources & evidence

ORD record
ord-1a6645b35a994819a75928e51b63f91b
Source dataset
uspto-grants-2012_01
Patent number
US08101623B2

Reaction notes

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