Hydrogen Peroxide → 6-(4-Propylphenyl)-3,4,5-trifluoro-2-naphthol

HRID 1350610Notes

Reaction equation

C([Li])CCC.CCCCCC.[CH2:12]([C:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH:30]=[CH:29][C:28]3[C:23](=[C:24]([F:32])[C:25]([F:31])=[CH:26][CH:27]=3)[C:22]=2[F:33])=[CH:17][CH:16]=1)[CH2:13][CH3:14].CI.[OH:36]O>O.C(O)(=O)C.O1CCCC1>[CH2:12]([C:15]1[CH:20]=[CH:19][C:18]([C:21]2[C:22]([F:33])=[C:23]3[C:28](=[CH:29][CH:30]=2)[CH:27]=[C:26]([OH:36])[C:25]([F:31])=[C:24]3[F:32])=[CH:17][CH:16]=1)[CH2:13][CH3:14]

Participants

Conditions

Temperature: 0 °C

Procedure

A 1.58 M butyllithium/hexane solution (16.4 ml) was added dropwise to a tetrahydrofuran (25 ml) solution of 2-(4-propylphenyl)-1,7,8-trifluoronaphthalene (6.5 g) at −65° C., and the reaction solution was stirred for 1 hour. A tetrahydrofuran (25 ml) solution of methyl iodide (3.7 g) was added dropwise to the reaction solution for 30 minutes, and then the reaction temperature was increased to 0° C. Acetic acid (1.85 ml) and 30% hydrogen peroxide (3 ml) were added to the reaction solution, followed by stirring for a while. Water was added to the reaction solution. The organic layer was removed, and the aqueous layer was extracted with ethyl acetate. The organic layers were combined, washed with water and brine, and concentrated. Then, 6-(4-propylphenyl)-3,4,5-trifluoro-2-naphthol was obtained.

Workup

stirringby stirring for a while
customThe organic layer was removed
extractionthe aqueous layer was extracted with ethyl acetate
washwashed with water and brine
concentrationconcentrated

Sources & evidence

ORD record: ord-a9ec29ce25be4e9ea8694f6d3886ed32
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07214835B2

Reaction notes

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