Sodium Hydroxide → 2-[2-(2-Chlorophenyl)ethenyl]-5-methyl-1,3-oxazole-4-carboxylic acid

HRID 746018Notes

Reaction equation

[Cl:1][C:2]1[CH:20]=[CH:19][CH:18]=[CH:17][C:3]=1[CH:4]=[CH:5][C:6]1[O:7][C:8]([CH3:16])=[C:9]([C:11]([O:13]CC)=[O:12])[N:10]=1.[OH-].[Na+]>C(O)C>[Cl:1][C:2]1[CH:20]=[CH:19][CH:18]=[CH:17][C:3]=1[CH:4]=[CH:5][C:6]1[O:7][C:8]([CH3:16])=[C:9]([C:11]([OH:13])=[O:12])[N:10]=1

Participants

Conditions

Temperature: 100 °C

Procedure

Ethyl 2-(2-chlorostyryl)-5-methyl-4-oxazolecarboxylate (6.0 g) was added to a mixture of ethanol (42 ml) and 2N sodium hydroxide (21 ml) and the whole mixture was heated on a water bath at 100° C. for dissolution. New crystals (sodium salt) immediately precipitated out. They were dissolved by addition of water and the solution was acidified with acetic acid to give 2-(2-chlorostyryl)-5-methyl-4-oxazolecarboxylic acid as crystals; yield 5.2 g (96.3%). Recrystallization from acetic acid-water gave colorless needles. melting at 223°-224° C.

Workup

customNew crystals (sodium salt) immediately precipitated out
dissolutionThey were dissolved by addition of water

Sources & evidence

ORD record: ord-969cc760bf834b2684b3181cf7d02025
Source dataset: uspto-grants-1986_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04602027

Reaction notes

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