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

HRID 1277273Notes

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-2884af7807d8496c816c6d6e553feb56
Source dataset: uspto-grants-2000_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06166006

Reaction notes

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