Hydrochloric Acid → 6-Carboxy-8-chloro-5-methylthiochroman-4-one

HRID 1275439Notes

Reaction equation

HRID 1275439 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:14]([O:16]CC)=[O:15])[C:5]([CH3:13])=[C:6]2[C:11]=1[S:10][CH2:9][CH2:8][C:7]2=[O:12].Cl>C(O)(=O)C.O>[C:14]([C:4]1[C:5]([CH3:13])=[C:6]2[C:11](=[C:2]([Cl:1])[CH:3]=1)[S:10][CH2:9][CH2:8][C:7]2=[O:12])([OH:16])=[O:15]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 109021585-Methyl-6-ethoxycarbonyl-8-chlorothiochroman-4-one

Product 1

HCID 221184346-Carboxy-8-chloro-5-methylthiochroman-4-oneYield 90%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

2.0 Grams (7.0 mmol) of 8-chloro-6-ethoxycarbonyl-5-methylthiochroman-4-one was dissolved in 10 ml of acetic acid, and 10 ml of a 4N hydrochloric acid aqueous solution was added. The mixture was refluxed under heat for 5 hours. After allowed to cool to room temperature, the reaction mixture was diluted with about 100 ml of water, and a precipitated solid was extracted with ethyl acetate. A carboxylic acid component was extracted from an organic layer with a saturated sodium hydrogencarbonate aqueous solution, and an aqueous layer was neutralized and acidified with a 5 wt % hydrochloric acid aqueous solution. A precipitated solid was extracted with ethyl acetate, and an organic layer was washed with a saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate. The solvent was distilled off to give 1.6 g (yield 90%) of 6-carboxy-8-chloro-5-methylthiochroman-4-one in the form of a white solid.

Workup

  1. temperatureThe mixture was refluxed
  2. temperatureunder heat for 5 hours
  3. extractiona precipitated solid was extracted with ethyl acetate
  4. extractionA carboxylic acid component was extracted from an organic layer with a saturated sodium hydrogencarbonate aqueous solution
  5. extractionA precipitated solid was extracted with ethyl acetate
  6. washan organic layer was washed with a saturated sodium chloride aqueous solution
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-548c19545f6c487d926b04868a60bc5f
Source dataset
uspto-grants-2000_12
Patent number
US06159904

Reaction notes

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