Sulfuric Acid → 7-Bromo-3-methylnaphthalen-1-ol

HRID 926202Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 926202
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([CH3:16])=[CH:10][C:11]([O:13]CC)=O)=[CH:4][CH:3]=1.OS(O)(=O)=O>>[Br:1][C:2]1[CH:3]=[C:4]2[C:5]([CH:8]=[C:9]([CH3:16])[CH:10]=[C:11]2[OH:13])=[CH:6][CH:7]=1

Komponenten

3

Edukt 2

HCID 1118Sulfuric AcidHCID 67126147Ethyl 4-(4-bromophenyl)-3-methylbut-2-enoate

Produkt 1

HCID 671262827-Bromo-3-methylnaphthalen-1-ol

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A flask containing the crude ethyl 4-(4-bromophenyl)-3-methylbut-2-enoate from above (˜30 grams) was treated with concentrated H2SO4 (120 mL) and warmed to 50° C. for 2.5 h. The reaction was poured onto ˜500 mL of crushed ice. Once the ice had thawed, the brown suspension was extracted with two portions of EtOAc (500 mL and 100 mL, respectively). The two extracts were combined, washed with saturated NaHCO3, dried (MgSO4), filtered, and concentrated to ˜55 mL. The residue was treated with DCM and loaded onto a silica gel column and purified by flash chromatography (ethyl acetate/hexanes) giving the desired product. 1H NMR (400 MHz, CDCl3) δ 8.29 (d, J=1.9 Hz, 1H), 7.57 (d, J=8.6 Hz, 1H), 7.50 (dd, J=8.6, 2.0 Hz, 1H), 7.17 (s, 1H), 6.67 (s, 1H), 2.42 (s, 3H).

Aufarbeitung

  1. extractionthe brown suspension was extracted with two portions of EtOAc (500 mL and 100 mL
  2. washwashed with saturated NaHCO3
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated to ˜55 mL
  6. additionThe residue was treated with DCM
  7. custompurified by flash chromatography (ethyl acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-8fd3423e43d84f62a31b1cf6b85b3afa
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09284323B2

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