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

HRID 647372Notes

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) δ 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 (ε2,910), 323 (2,645), 297 (4,440), 286 (4,880), 236 (30,050), 224 (46,730).

Workup

customthe solid in the reaction mixture was 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-57d685f0e7ee4cf4bd9f1d76a0b25571
Source dataset: uspto-grants-1983_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04408077

Reaction notes

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