Acetic Acid → 4,4'-Dihydroxybenzil

HRID 1164247

Reaktionsgleichung

Reaktionsgleichung von HRID 1164247
[C:1]1([C:9]([C:11]([C:13]2[CH:20]=[CH:19][C:16]([O:17]C)=[CH:15][CH:14]=2)=[O:12])=[O:10])[CH:8]=[CH:7][C:4]([O:5]C)=[CH:3][CH:2]=1.C1(C(C(C2C=CC(OC)=CC=2)O)=O)C=CC(OC)=CC=1.C(O)(=O)C.Br>N1C=CC=CC=1.S([O-])([O-])(=O)=O.[Cu+2]>[OH:5][C:4]1[CH:3]=[CH:2][C:1]([C:9]([C:11]([C:13]2[CH:14]=[CH:15][C:16]([OH:17])=[CH:19][CH:20]=2)=[O:12])=[O:10])=[CH:8][CH:7]=1

Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 710434,4'-Dimethoxybenzil2×HCID 954154,4'-Dimethoxybenzoin

Produkt 1

HCID 4582044,4'-DihydroxybenzilAusbeute 94,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24462Copper SulfateKatalysatorHCID 1049PyridineLösungsmittel

Versuchsvorschrift

Anisil (6.5 g), made by the oxidation of anisoin with copper sulphate in pyridine, was added to acetic acid (50 g) and heated to reflux to form a solution. Hydrobromic acid (s.g. 1.48) was added at reflux until anisil just started to precipitate (about 30 ml HBr being needed). After 2 hours' reflux, more hydrobromic acid (50 ml) was added, and the solution was refluxed for a further 2 hours. After this time, thin layer chromatography showed complete conversion into a single product. The solution was poured into cold water (600 ml) to precipitate a white solid. This was filtered off, washed with water and dried to give 5.5 g of 4,4'-dihydroxybenzil. This was used without further purification.

Aufarbeitung

  1. temperatureheated
  2. temperatureto reflux
  3. customto form a solution
  4. customto precipitate (about 30 ml HBr being needed)
  5. temperatureAfter 2 hours' reflux
  6. additionmore hydrobromic acid (50 ml) was added
  7. temperaturethe solution was refluxed for a further 2 hours
  8. additionThe solution was poured into cold water (600 ml)
  9. customto precipitate a white solid
  10. filtrationThis was filtered off
  11. washwashed with water
  12. customdried

Quellen und Nachweise

ORD-Eintrag
ord-a5715372696e4e25ae98b05f295115d0
Quelldatensatz
uspto-grants-1983_01
Patentnummer
US04368253

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