Sulfuric Acid → 4-(2'-Methoxyethoxy)-2-methyl-1-naphthol

HRID 1003123

Reaktionsgleichung

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

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

4.9g of concentrated sulfuric acid were added dropwise, with stirring, to a mixture of 4.75 g (27.6 mmole) of 2-methyl-1,4-naphthoquinone, 2.71 g (41.4 mmole) of zinc powder, 15 mL of 2-methoxyethanol and 15 mL of toluene, in an ice bath. After the addition was completed, the reaction mixture was stirred for 5 hours at 100° C. The reaction product was extracted with ethyl acetate, washed with water, then brine, dried over sodium sulfate, filtered, then evaporated under reduced pressure to give 4.87 g (76% yield) of the title compound. The resultant product had a melting point of 100-101° C. and an 1HNMR as follows: (300 Hz, DMSO-d6) δ 2.33 (s, 3H), 3.34 (s, 3H), 3.79 (t, 2H, J=4.5 Hz), 4.21 (t, 2H, J=4.5 Hz), 6.78(s, 1H), 7.47 (m, 2H), 8.08 (d, 1H, J=8.0 Hz), 8.14 (d, 1H, J=8.0 Hz), 8.54 (s, 1H). The mass spectrum showed a molecular ion at m/z 232.

Aufarbeitung

additionAfter the addition
extractionThe reaction product was extracted with ethyl acetate
washwashed with water
dry with materialbrine, dried over sodium sulfate
filtrationfiltered
customevaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag: ord-a56c081f340f4d13bbd2530e7e99a1fc
Quelldatensatz: uspto-grants-2000_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06045590

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