2'-Methyl-biphenyl-2,4'-dicarboxylic acid → 4-methyl-9-oxo-9H-fluorene-2-carboxylic acid

HRID 1799022Notes

Reaction equation

[CH3:1][C:2]1[CH:7]=[C:6]([C:8]([OH:10])=[O:9])[CH:5]=[CH:4][C:3]=1[C:11]1[C:12]([C:17](O)=[O:18])=[CH:13][CH:14]=[CH:15][CH:16]=1>O>[CH3:1][C:2]1[C:3]2[C:11]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:17](=[O:18])[C:4]=2[CH:5]=[C:6]([C:8]([OH:10])=[O:9])[CH:7]=1

Participants

Conditions

Temperature: 180 °C

Procedure

A mixture of 2′-methyl-biphenyl-2,4′-dicarboxylic acid (1.94 g) and polyphosphoric acid (50 g) was stirred at 180° C. for 3 hr. The reaction mixture was cooled to room temperature, water (100 ml) was slowly added dropwise, and the mixture was further stirred at room temperature for 10 min. This suspension was filtered, and the obtained solid was successively washed with water (50 ml) and 50 v/v % aqueous methanol solution (50 ml). The obtained solid was air-dried, and dried under reduced pressure at 80° C. to give the title compound (1.745 g, 97%).

Workup

temperatureThe reaction mixture was cooled to room temperature
stirringthe mixture was further stirred at room temperature for 10 min
filtrationThis suspension was filtered
washthe obtained solid was successively washed with water (50 ml) and 50 v/v % aqueous methanol solution (50 ml)
customThe obtained solid was air-dried
customdried under reduced pressure at 80° C.

Sources & evidence

ORD record: ord-bde43fa7d41d4710b1696f6d41905484
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08343994B2

Reaction notes

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