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

HRID 2300673Notes

Reaction equation

HRID 2300673 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 1 N 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, 2 N 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
  2. waitfor 30 minutes at room temperature
  3. customthe crystals thus precipitated
  4. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-7d497bcd52f242e299e3acef84426678
Source dataset
uspto-grants-2002_12
Patent number
US06498179B1

Reaction notes

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