Sodium Hydroxide → 6-(4-methylphenyl)-2H-thiochromene-3-carboxylic acid

HRID 566099Notes

Reaction equation

[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][CH:17]=2)[S:14][CH2:13][C:12]([C:18]([O:20]CC)=[O:19])=[CH:11]3)=[CH:4][CH:3]=1.[OH-].[Na+]>O1CCCC1.C(#N)C>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][CH:17]=2)[S:14][CH2:13][C:12]([C:18]([OH:20])=[O:19])=[CH:11]3)=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of ethyl 6-(4-methylphenyl)-2H-thiochromene-3-carboxylate (2.12 g, 6.84 mmol) in tetrahydrofuran (20 ml) and acetonitrile (20 ml) was added dropwise 1N sodium hydroxide (7 ml), and the mixture was stirred at 60° C. for 2.5 hours. The solvent was evaporated, and the residue was dissolved in diethylether. The mixture was extracted with water. The organic layer was extracted with 0.5N sodium hydroxide, and both of the aqueous layers were made pH 3 with 6N hydrochloric acid. The mixture was extracted with ethyl acetate, and the organic layer was washed with saturated brine and dried with magnesium sulfate. The solvent was evaporated to give 6-(4-methyl-phenyl)-2H-thiochromene-3-carboxylic acid (1.83 g, 95%) as yellow powder.

Workup

customThe solvent was evaporated
dissolutionthe residue was dissolved in diethylether
extractionThe mixture was extracted with water
extractionThe organic layer was extracted with 0.5N sodium hydroxide
extractionThe mixture was extracted with ethyl acetate
washthe organic layer was washed with saturated brine
dry with materialdried with magnesium sulfate
customThe solvent was evaporated

Sources & evidence

ORD record: ord-a86ea63d0d084503b4a3a6c8ac90efbb
Source dataset: uspto-grants-2001_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06172061B2

Reaction notes

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