Hydrochloric Acid → 3-(2-Methoxyphenyl)-5-methyl-1,2-oxazole-4-carboxylic acid

HRID 1808860Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:13]([C:14]([O:16]CC)=[O:15])=[C:12]([CH3:19])[O:11][N:10]=1.[OH-].[Na+].CCOCC.Cl>CO.O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:13]([C:14]([OH:16])=[O:15])=[C:12]([CH3:19])[O:11][N:10]=1

Participants

Conditions

Temperature: 65 °C

Procedure

The reaction mixture of ethyl 3-(2-methoxyphenyl)-5-methylisoxazole-4-carboxylate (12.85 g, 49.2 mmol) and sodium hydroxide (9.84 g, 246 mmol) in MeOH (100 mL) and Water (10 mL) in a 500-mL round bottom flask was stirred at 65° C. for 20 hours. The MeOH was removed in vacuo, then the concentrated reaction mixture was transferred to a 500-mL separatory funnel with 150 mL of water and 100 mL of ether. The organic layer was discarded. The aqueous layer was acidified by adding concentrated HCl (26 mL). The product precipitated and was separated by filtration and dried under high vacuum to give 10.63 g (93%, theoretical yield 11.47 g). 1H NMR (400 MHz, CD3OD) δ 2.69 (s, 3H, CH3), 3.77 (s, 3H, OCH3), 7.00-7.07 (m, 2H, aryl), 7.32-7.34 (m, 1H, aryl), 7.43-7.48 (m, 1H, aryl).

Workup

customThe MeOH was removed in vacuo
customthe concentrated reaction mixture
customThe product precipitated
customwas separated by filtration
customdried under high vacuum
customto give 10.63 g (93%, theoretical yield 11.47 g)

Sources & evidence

ORD record: ord-1845599ebd854fc8805a7a3ff01f3896
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08362004B2

Reaction notes

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