Hydrochloric Acid → 6-(2-Chlorophenyl)-4-oxo-4H-pyran-2-carboxylic acid

Reaction equation

Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:13][C:12]([C:14]([O:16]CC)=[O:15])=[CH:11][C:10](=[O:19])[CH:9]=2)=[CH:4][CH:3]=1.[ClH:20]>>[Cl:20][C:6]1[CH:7]=[CH:2][CH:3]=[CH:4][C:5]=1[C:8]1[O:13][C:12]([C:14]([OH:16])=[O:15])=[CH:11][C:10](=[O:19])[CH:9]=1

Participants

Reactant 2

HCID 313Hydrochloric Acid

HCID 550407Ethyl 6-(4-chlorophenyl)-4-oxo-4H-pyran-2-carboxylate

Product 1

HCID 155783816-(2-Chlorophenyl)-4-oxo-4H-pyran-2-carboxylic acid

Procedure

A mixture of ethyl 6-(4-chlorophenyl)-4-oxo-4H-pyran-2-carboxylate (3.9 g) and concentrated hydrochloric acid (40 ml) was heated under reflux for 2 hours. The reactant dissolved on warming and a solid began to precipitate. Water (40 ml) was added to the cooled mixture and the resulting buff solid yielded the title product as off-white needles (mp 241°-246° C. with decomposition).

Workup

temperaturewas heated
temperatureunder reflux for 2 hours
dissolutionThe reactant dissolved
temperatureon warming
customto precipitate
additionWater (40 ml) was added to the cooled mixture

Sources & evidence

ORD record: ord-d99296df734f4604afff7b50eda18bce
Source dataset: uspto-grants-1984_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04448787

Reaction notes

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