Hydrochloric Acid → 2-Chloro-4-(4-chlorophenyl)-5-oxazolepropionic acid

HRID 567165Notes

Reaction equation

HRID 567165 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[O:5][C:6]([CH2:16][CH2:17][C:18]([O:20]C)=[O:19])=[C:7]([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=2)[N:8]=1.Cl>C(O)C>[Cl:3][C:4]1[O:5][C:6]([CH2:16][CH2:17][C:18]([OH:20])=[O:19])=[C:7]([C:9]2[CH:10]=[CH:11][C:12]([Cl:15])=[CH:13][CH:14]=2)[N:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 10990225Methyl 3-[2-chloro-4-(4-chlorophenyl)-5-oxazolyl]propionate

Product 1

HCID 118082582-Chloro-4-(4-chlorophenyl)-5-oxazolepropionic acidYield 99%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

An aqueous solution of 1N sodium hydroxide (34 ml) was dropwise added to an ethanol (50 ml) solution of methyl 2-chloro-4-(4-chlorophenyl)-5-oxazolepropionate (8.50 g), with cooling with ice. After stirring for 20 minutes with cooling and then for 30 minutes at room temperature, 2N hydrochloric acid was added thereto, and the crystals thus precipitated were collected by filtration to obtain 2-chloro-4-(4-chlorophenyl)-5-oxazolepropionic acid (8.00 g, 99%). This was recrystallized from ethyl acetate to give colorless prisms. mp 169-170° C.

Workup

  1. temperaturewith cooling with ice
  2. temperaturewith cooling
  3. waitfor 30 minutes at room temperature
  4. customthe crystals thus precipitated
  5. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-df4493d518164ec58788f920a1e08d67
Source dataset
uspto-grants-2001_01
Patent number
US06177452B1

Reaction notes

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