Sulfamic Acid → 3-Cyclopentyloxy-6-fluoro-4-methoxybenzoic acid

HRID 1825383Notes

Reaction equation

[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([C:12]([F:17])=[CH:13][C:14]=2[O:15][CH3:16])[CH:10]=[O:11])[CH2:5][CH2:4][CH2:3][CH2:2]1.S(=O)(=O)([OH:20])N.Cl([O-])=O.[Na+]>C(O)(=O)C.O>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([C:12]([F:17])=[CH:13][C:14]=2[O:15][CH3:16])[C:10]([OH:20])=[O:11])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 3-cyclopentyloxy-6-fluoro-4-methoxybenzaldehyde (1.4 g) in glacial acetic acid (20 mL) is treated with sulfamic acid (0.82 g) at room temperature and stirred for 10 minutes. The resulting yellow solution is cooled to 0° C. and treated with a solution of sodium chlorite (0.69 g of an 80% pure sample) in water (20 mL) during 10 minutes. The resulting yellow suspension is stirred at room temperature for 3 hours, poured into water (100 mL) and filtered to give 3-cyclopentyloxy-6-fluoro-4-methoxybenzoic acid (0.88 g), in the form of a white solid. [NMR (CDCl3):—7.46(d,1H,J=8 Hz),6.65(d,1H,J=12 Hz), 4.80–0.76 (m, 1H), 3.90(s,3H), 2.01–1.58(m,8H)].

Workup

stirringThe resulting yellow suspension is stirred at room temperature for 3 hours
filtrationfiltered

Sources & evidence

ORD record: ord-de66feabf7e34f86b51b6820da3783fd
Source dataset: uspto-grants-2006_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07045660B2

Reaction notes

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