Hydrochloric Acid → 3-[4-(4-Chlorophenyl)-2-methyl-1,3-oxazol-5-yl]propanoic acid

HRID 1982440Notes

Reaction equation

HRID 1982440 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:11]=[C:12]([CH3:21])[O:13][C:14]=2[CH2:15][CH2:16][C:17]([O:19]C)=[O:18])=[CH:6][CH:5]=1.Cl>C(O)C.O>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[N:11]=[C:12]([CH3:21])[O:13][C:14]=2[CH2:15][CH2:16][C:17]([OH:19])=[O:18])=[CH:8][CH:9]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 13293290Methyl 3-[4-(4-chlorophenyl)-2-methyl-1,3-oxazol-5-yl]propanoate

Product 1

HCID 132932823-[4-(4-Chlorophenyl)-2-methyl-1,3-oxazol-5-yl]propanoic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

2N Sodium hydroxide (5 ml) was added to a solution of methyl 4-(4-chlorophenyl)-2-methyloxazole-5-propionate (1.4 g) in ethanol (10 ml) and the mixture was allowed to stand at room temperature for 30 minute, diluted with water and adjusted to pH 2 with hydrochloric acid. The resulting crystalline precipitate was collected by filtration and recrystallized from ethanol to give crystals of 4-(4-chlorophenyl)-2-methyloxazole-5-propionic acid, yield 1.17 g (88.6%), m.p. 211°-212° C. The IR and NMR spectra of this compound were in complete agreement with those of the compound obtained in Example 5.

Workup

  1. filtrationThe resulting crystalline precipitate was collected by filtration
  2. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-7184d8f7cd854388baa2a0dda0f43484
Source dataset
uspto-grants-1986_06
Patent number
US04596816

Reaction notes

Loading…