Sodium Hydroxide → HCID 68862086, Verbindung

HRID 871195

Reaktionsgleichung

Reaktionsgleichung von HRID 871195
[Br:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([Br:10])[C:3]=1[CH:4]=[O:5].[CH:11](O)([OH:14])[CH2:12][CH3:13].C(OC(OCC)OCC)C.[OH-].[Na+]>C(Cl)Cl.[Cl-].[Cl-].[Cl-].[Cl-].[Zr+4]>[Br:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([Br:10])[C:3]=1[CH:4]1[O:14][CH2:11][CH2:12][CH2:13][O:5]1

Komponenten

7

Edukt 4

HCID 14798Sodium HydroxideHCID 31214Ethyl orthoformateHCID 134919PropanediolHCID 126486412,6-Dibromobenzaldehyde

Produkt 1

HCID 68862086HCID 68862086, VerbindungAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9856075Zirconium chloride (ZrCl4), (T-4)-KatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

2,6-Dibromobenzaldehyde (49) (10.0 g, 37.9 mmol) was dissolved in 160 ml dry CH2Cl2. Propanediol (6.4 ml, 88.5 ml), triethylorthoformate (6.83 ml, 41 mmol) and anhydrous ZrCl4 (1.0 g) were added at ambient temperature and stirred overnight. Then NaOH (50 ml of a 10% solution) was added and stirred for an additional hour. The organic phase was separated, the aqueous phase was extracted with Et2O (2×40 ml). The combined organic phases were washed with water (3×60 ml), dried over MgSO4 and the volatiles were removed in vacuo to afford 12 g (98%) 2-(2,6-Dibromophenyl)-1,3-dioxane (acetal) as a slightly yellow solid.

Aufarbeitung

  1. stirringstirred for an additional hour
  2. customThe organic phase was separated
  3. extractionthe aqueous phase was extracted with Et2O (2×40 ml)
  4. washThe combined organic phases were washed with water (3×60 ml)
  5. dry with materialdried over MgSO4
  6. customthe volatiles were removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-39a49ebe1c9f419c8d447ac9182f1073
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08969624B2

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