Ethylene Glycol → 4-(2'-Hydroxyethoxy)-2-methyl-1-hydroxynaphthalene

HRID 1003122

Reaktionsgleichung

Reaktionsgleichung von HRID 1003122
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.[CH2:19](O)[CH2:20][OH:21]>[Zn].C1(C)C=CC=CC=1>[OH:21][CH2:20][CH2:19][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

6

Edukt 3

HCID 174Ethylene GlycolHCID 1118Sulfuric AcidHCID 4055Menadione

Produkt 1

HCID 158473234-(2'-Hydroxyethoxy)-2-methyl-1-hydroxynaphthaleneAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23994ZincKatalysatorHCID 1140TolueneLösungsmittel

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) 2-methyl-1,4 naphthoquinone, 2.71 g (41.4 mmole) of zinc powder, 15 mL of ethylene glycol and 15 mL of toluene in an ice bath. After the addition was complete, the reaction mixture was stirred for 5 hours at 100° C. The reaction product was extracted with ethyl acetate, washed with water, brine, dried over sodium sulfate, filtered, then evaporated under reduced pressure to give 4.21 g (70% yield) of the above product. That product had a melting point of 136.3-136.8° C. and an 1HNMR as follows: (300 MHz, DMSO-d6) δ 2.37 (s, 3H), 3.86 (m, 2H), 4.10 (t, 2H, J=4.8 Hz), 4.98 (t, 1H, J=5.4 Hz), 6.76 (s, 1H), 7.42 (m, 2H), 8.14 (d, 1H, J=9.0 Hz), 8.17 (d, 1H, J=9.0 Hz), 8.51 (s, 1H). The mass spectrum showed a molecular ion at m/z 218.

Aufarbeitung

  1. additionAfter the addition
  2. extractionThe reaction product was extracted with ethyl acetate
  3. washwashed with water, brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-55b90b1bffb049339a18b2891379a7c2
Quelldatensatz
uspto-grants-2000_04
Patentnummer
US06045590

Verknüpfte Notizen

Wird geladen…