Acetic Acid → [1,1'-Biphenyl]-4,4'-dicarboxaldehyde

HRID 1392573

Reaktionsgleichung

Reaktionsgleichung von HRID 1392573
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([CH2:15][OH:16])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.C(O)(=O)C.Br([O-])(=O)=O.[Na+].BrBr>O>[CH:15]([C:12]1[CH:11]=[CH:10][C:9]([C:6]2[CH:7]=[CH:8][C:3]([CH:2]=[O:1])=[CH:4][CH:5]=2)=[CH:14][CH:13]=1)=[O:16]

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 24408BromineHCID 6117864,4'-Bis(hydroxymethyl)biphenylHCID 23668195Sodium Bromate

Produkt 1

HCID 6200[1,1'-Biphenyl]-4,4'-dicarboxaldehydeAusbeute 101,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel2×

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

In a 50 ml three-necked flask equipped with a magnetic stirrer, a reflux condenser and a thermometer, 4.28 g (20 mmols) of 4,4′-bishydroxymethylbiphenyl and 10 ml of (166 mmols) of acetic acid were charged, followed by heating to 75° C. An aqueous solution prepared by dissolving 2.04 g (13.5 mmols) of sodium bromate in 10 ml of water was added dropwise, and then the mixture was stirred at 75° C. until a color of bromine disappears. To the system, 50 ml of water was added and, after filtration, the resulting substance was dried to obtain 4.25 g of 4,4′-bisformylbiphenyl as a white crystal. Yield: 99.9%. It was confirmed by GS-MS that a molecular ion peak is 209.

Aufarbeitung

  1. customIn a 50 ml three-necked flask equipped with a magnetic stirrer, a reflux condenser
  2. customAn aqueous solution prepared
  3. additionwas added dropwise
  4. filtrationafter filtration
  5. customthe resulting substance was dried

Quellen und Nachweise

ORD-Eintrag
ord-d324fd50163441b1ba9520051179fd69
Quelldatensatz
uspto-grants-2008_03
Patentnummer
US07342138B2

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