Hexane → HCID 22398285, Verbindung

HRID 1070886Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1070886
[CH3:1][C:2]1([CH3:13])[C:10]2[C:5](=[CH:6][C:7]([CH3:12])=[C:8]([OH:11])[CH:9]=2)[CH2:4][CH2:3]1.[Br:14]Br.C(OCC)(=O)C.CCCCCC>C(O)(=O)C>[Br:14][C:9]1[C:8]([OH:11])=[C:7]([CH3:12])[CH:6]=[C:5]2[C:10]=1[C:2]([CH3:13])([CH3:1])[CH2:3][CH2:4]2

Komponenten

6

Edukt 4

HCID 8058HexaneHCID 8857Ethyl AcetateHCID 24408BromineHCID 30175493,3,6-Trimethyl-2,3-dihydro-1H-inden-5-ol

Produkt 1

HCID 22398285HCID 22398285, VerbindungAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a 25 mL one necked round bottom flask, 3,3,6-trimethylindan-5-ol was dissolved in acetic acid (10 mL). The solution was cooled down to 0° C. followed by slow addition of bromine (290 μL, 5.65 mmol). The reaction was slowly warmed up to room temperature. After 3 h of stirring, the reaction was completed. Excess acetic acid was removed by rotavap, and the residue was quenched with ascorbic acid solution. The content was extracted with sodium bicarbonate and brine. Plugged column with silica gel 5:95 ethyl acetate:hexane gave colorless oil, 4-bromo-3,3,6-trimethylindan-5-ol (82% yield). 1H NMR (300 MHz, CDCl3): δ 1.42 (s, 6H), 1.98(dd, 2H, J=15.11, 7.55 Hz), 2.24 (s, 3H), 2.54 (s, 3H), 2.57 (s, 3H), 2.85(d, 2H, J=7.55 Hz), 3.89 (s, 3H), 5.12(d, 1H, J=3.40 Hz), 6.31 (s, 1H), 6.95(m, 1H), 7.01 (s, 1H), 7.12(d, 1H, J=3.40) 8.34 (bs, 1H).

Aufarbeitung

  1. temperatureThe reaction was slowly warmed up to room temperature
  2. customExcess acetic acid was removed by rotavap
  3. customthe residue was quenched with ascorbic acid solution
  4. extractionThe content was extracted with sodium bicarbonate and brine

Quellen und Nachweise

ORD-Eintrag
ord-2019061d661243d8b8bf604d92fa643e
Quelldatensatz
uspto-grants-2005_06
Patentnummer
US06903132B2

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