Sulfuric Acid → 3,4-dihydro-1-hydroxy-5-methyl-1-(trifluoromethyl)-2(1H)-naphthalenone oxime

HRID 647370Notes

Reaction equation

OS(O)(=O)=O.[F:6][C:7]([F:23])([F:22])[C:8](=[O:21])[C:9](=[N:19][OH:20])[CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH3:18]>C1(C)C=CC=CC=1>[OH:21][C:8]1([C:7]([F:22])([F:23])[F:6])[C:17]2[C:12](=[C:13]([CH3:18])[CH:14]=[CH:15][CH:16]=2)[CH2:11][CH2:10][C:9]1=[N:19][OH:20]

Participants

Conditions

Temperature: 25 °C

Procedure

Cold concentrated H2SO4 (12 ml, 98% w/v H2SO4 in water) was added to a stirred suspension of 1,1,1-trifluoro-5-(2-methylphenyl)-2,3-pentanedione 3-oxime (11.9 g, 45.9 mmol) in toluene (16 mL) at 0° C. The reaction mixture and allowed to warm to room temperature (25° C.) and then stirred for 30 min. Ice was added to the reaction mixture. The resulting mixture was extracted with diethyl ether (2x). The ether extract was washed successively with water and a saturated aqueous solution of NaHCO3, dried (MgSO4) and concentrated under reduced pressure to give the title compound (10.4 g, 87% yield). This product was used for the reaction described in the following example. A small sample was triturated with hexane to give-off white crystals; mp 154°-156° C.; nmr (CDCl3) δ 2.3 (s, 3H), 2.9 (m, 4H), 7.2 (m, 2H), 7.6 (m, 1H); ir (CHCl3) 3570, 3480, 1170 cm-1 ; uvλmax (MeOH) 273 nm (ε570), 266 (590).

Workup

additionIce was added to the reaction mixture
extractionThe resulting mixture was extracted with diethyl ether (2x)
extractionThe ether extract
washwas washed successively with water
dry with materiala saturated aqueous solution of NaHCO3, dried (MgSO4)
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-8d703aee5c43483b987877f8540af272
Source dataset: uspto-grants-1983_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04408077

Reaction notes

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