Hydrogen Bromide → 2-Bromo-1-(2,3-dihydro-1,4-benzodioxin-2-yl)ethan-1-ol

HRID 225145Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 225145
[Br:1][CH2:2][C:3]([CH:5]1[O:10][C:9]2[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=2[O:7][CH2:6]1)=[O:4].[BH4-].[Na+].Br>CO>[O:10]1[C:9]2[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=2[O:7][CH2:6][CH:5]1[CH:3]([OH:4])[CH2:2][Br:1]

Komponenten

5

Edukt 3

HCID 260Hydrogen BromideHCID 4311764Sodium borohydrideHCID 126085852-Bromo-1-(2,3-dihydro-1,4-benzodioxin-2-yl)ethan-1-one

Produkt 1

HCID 126085902-Bromo-1-(2,3-dihydro-1,4-benzodioxin-2-yl)ethan-1-olAusbeute 25,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
-70 °C

Versuchsvorschrift

2-Bromoacetyl-1,4-benzodioxan(53.8 g) in methanol (500 mls) was cooled to -70° C. Sodium borohydride (10.3 g) was added and the solution stirred at -70° C. for 12 hours. The solution was treated with hydrobromic acid until acidic and the solvent evaporated. The residue was dissolved in ether and the ether extracts were washed with sodium bicarbonate solution; then water and dried (MgSO4) and evaporated to give a white solid. This was recrystallised eight times from petroleum spirit 60-80 to give 14 grams of the title compound.

Aufarbeitung

  1. customevaporated
  2. dissolutionThe residue was dissolved in ether
  3. washthe ether extracts were washed with sodium bicarbonate solution
  4. dry with materialthen water and dried (MgSO4)
  5. customevaporated
  6. customto give a white solid
  7. customThis was recrystallised eight times from petroleum spirit 60-80

Quellen und Nachweise

ORD-Eintrag
ord-49ade3456d8649a7ba63b43f907aac16
Quelldatensatz
uspto-grants-1980_11
Patentnummer
US04235915

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