Pyridinium chloride → 5-(3-Carboxybenzoyl)-2-hydroxybenzenepropanoic acid

HRID 981845Notes

Reaction equation

C([O:3][C:4]([C:6]1[CH:7]=[C:8]([CH:26]=[CH:27][CH:28]=1)[C:9]([C:11]1[CH:12]=[CH:13][C:14]([O:24]C)=[C:15]([CH2:17][CH2:18][C:19]([O:21]CC)=[O:20])[CH:16]=1)=[O:10])=[O:5])C.Cl.N1C=CC=CC=1>O>[C:4]([C:6]1[CH:7]=[C:8]([CH:26]=[CH:27][CH:28]=1)[C:9]([C:11]1[CH:12]=[CH:13][C:14]([OH:24])=[C:15]([CH2:17][CH2:18][C:19]([OH:21])=[O:20])[CH:16]=1)=[O:10])([OH:5])=[O:3]

Participants

Conditions

Temperature: 180 °C

Procedure

A mixture of 41.5 g of 5-[3-(ethoxycarbonyl)benzoyl]-2-methoxybenzenepropanoic acid, ethyl ester and 410 g of pyridine hydrochloride were heated at 180° C. for 4 hours. After cooling, water was added to the mixture while hot. As the mixture cooled, the title product precipitated from solution. Filtration of the solids and crystallization from ethanol/water provided 31.1 g of the title product, m.p. 197°-200° C.

Workup

temperatureAfter cooling
temperatureAs the mixture cooled
customthe title product precipitated from solution
filtrationFiltration of the solids and crystallization from ethanol/water

Sources & evidence

ORD record: ord-8957998f52a5460e8715a4b9bf91f0ad
Source dataset: uspto-grants-1991_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04992576

Reaction notes

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