Potassium Permanganate → 7-Fluoro-2,3-dihydrobenzo[b][1,4]dioxine-6-carboxylic acid

HRID 1518022Notes

Reaction equation

[O-:1][Mn](=O)(=O)=O.[K+].[F:7][C:8]1[C:9]([CH:18]=[O:19])=[CH:10][C:11]2[O:16][CH2:15][CH2:14][O:13][C:12]=2[CH:17]=1>O>[F:7][C:8]1[C:9]([C:18]([OH:1])=[O:19])=[CH:10][C:11]2[O:16][CH2:15][CH2:14][O:13][C:12]=2[CH:17]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of KMnO4 (0.35 g, 2.2 mmol) in H2O (11 mL) at 80° C. was added 7-fluoro-2,3-dihydro-benzo[1,4]dioxine-6-carbaldehyde (0.20 g, 1.1 mmol). The resulting suspension was stirred at 100° C. for 24 h. The reaction mixture was filtered and the solids were washed with H2O (30 mL). The filtrate was acidified with concentrated HCl, which led to the formation of a white precipitate, which was collected, washed with H2O and dried in vacuo to provide 0.12 g (57%) of the title compound as a white solid. MS (ESI): exact mass calculated for C9H7FO4, 198.03; m/z not found. 1H NMR (400 MHz, DMSO-d6): 12.95 (s, 1H), 7.29 (d, J=7.2, 1H), 6.87 (d, J=11.6, 1H), 4.34-4.31 (m, 2H), 4.27-4.24 (m, 2H).

Workup

filtrationThe reaction mixture was filtered
washthe solids were washed with H2O (30 mL)
customwas collected
washwashed with H2O
customdried in vacuo

Sources & evidence

ORD record: ord-e590d7aed2c54e888f55d9ac4b768d08
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08232391B2

Reaction notes

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