2-Methoxybenzene-1,3,5-tricarboxylic acid → 2-Hydroxybenzene-1,3,5-tricarboxylic acid

HRID 1038286Notes

Reaction equation

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

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of 2-methoxy-benzene-1,3,5-tricarboxylic acid (3) (24 g, 0.1 mol) and 48% HBr (500 mL) was placed in a 1 L bound bottom flask. The reaction mixture was heated to reflux at 150° C. for 48 h. The progress of the deprotection was monitored by proton NMR. When the reaction was complete, the hydrobromic acid was removed under reduced pressure, and the residue was mixed with small amount of water. The deprotected triacid (13) was collected by filtration; yield 17 grams (75%).

Workup

temperatureThe reaction mixture was heated
customthe hydrobromic acid was removed under reduced pressure
additionthe residue was mixed with small amount of water
filtrationThe deprotected triacid (13) was collected by filtration

Sources & evidence

ORD record: ord-288f256b863b4c629153d32ff79945c7
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08551453B2

Reaction notes

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