Dimethyl Sulfate → 2-Methoxy-5-methyl-1-(trifluoromethyl)naphthalene

HRID 615519Notes

Reaction equation

[CH3:1]OS(OC)(=O)=O.[CH3:8][C:9]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:10]=1[CH:11]=[CH:12][C:13]([OH:23])=[C:14]2[C:19]([F:22])([F:21])[F:20].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:1][O:23][C:13]1[CH:12]=[CH:11][C:10]2[C:15](=[CH:16][CH:17]=[CH:18][C:9]=2[CH3:8])[C:14]=1[C:19]([F:20])([F:21])[F:22]

Participants

Conditions

Temperature: 25 °C

Procedure

Dimethylsulfate (1.13 g, 8.75 mmol, 0.85 mL) was added to a stirred suspension of 5-methyl-1-(trifluoromethyl)-2-naphthalenol (1.8 g, 7.96 mmol) and potassium carbonate (2.2 g, 15.9 mmol) in dimethylformamide (20 mL). After stirring the reaction mixture for 2 hr at 25° C. the solid in the reaction mixture was removed by filtration. The filtrate was extracted with hexane (400 mL). The extract was washed with brine, dried (MgSO4) and concentrated to dryness giving 1.7 g (90% yield) of the title compound. This product was used for the reaction described in the next example. A sample of the product, recrystallized from hexane, had mp 70°-71° C.; nmr (CDCl3) 67 2.65 (s, 3H), 3.95 (s, 3H), 7.2 (m, 2H), 7.35 (q, J=8 Hz, 1H), 8.0 (m, 1H), 8.1 (d, J=9 Hz, 1H); ir (CHCl3) 1390, 1340, 1280, 1255, 1245, 1110, 1095, 1085, 1045 cm-1 ; uvλmax (MeOH) 336 nm (ε 2,910), 323 (2,645), 297 (4,440), 286 (4,880), 236 (30,050), 224 (46,730).

Workup

customwas removed by filtration
extractionThe filtrate was extracted with hexane (400 mL)
washThe extract was washed with brine
dry with materialdried (MgSO4)
concentrationconcentrated to dryness

Sources & evidence

ORD record: ord-fdf936f284b24136ab501a579d9ec4c4
Source dataset: uspto-grants-1985_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04499310

Reaction notes

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