Citric Acid → Veratryl alcohol

HRID 377095

Reaktionsgleichung

Reaktionsgleichung von HRID 377095
P([O-])([O-])(O)=O.[K+].[K+].C(O)(=O)CC(CC(O)=O)(C(O)=O)[OH:11].P([O-])(O)(O)=O.[K+].C(O)(=O)CC(CC(O)=O)(C(O)=O)[OH:30].[CH3:40][O:41][C:42]1[CH:43]=[C:44]([CH3:50])[CH:45]=[CH:46][C:47]=1[O:48][CH3:49].CCN1C2C=CC(S([O-])(=O)=O)=CC=2S/C/1=N\N=C1/SC2C=C(S([O-])(=O)=O)C=CC=2N/1CC.[NH4+].[NH4+]>C(O)C>[CH3:40][O:41][C:42]1[CH:43]=[C:44]([CH:45]=[CH:46][C:47]=1[O:48][CH3:49])[CH:50]=[O:11].[CH3:40][O:41][C:42]1[CH:43]=[C:44]([CH:45]=[CH:46][C:47]=1[O:48][CH3:49])[CH2:50][OH:30]

Komponenten

8

Edukt 5

HCID 311Citric AcidHCID 681263,4-DimethoxytolueneHCID 516951Monobasic potassium phosphateHCID 95704746-benzothiazolesulfonic acid, 2,2'-azinobis(3-ethyl-2,3-dihydro-, diammonium saltHCID 21698641Dipotassium hydrogen phosphate citric acid

Produkt 2

HCID 7118Veratryl alcoholHCID 8419Veratraldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

22 ml of a dipotassium hydrogen phosphate/citric acid buffer solution of pH 4.5 (prepared by titrating a 0.2 M potassium dihydrogen phosphate solution with a 0.1 M citric acid solution and diluting to 1/4) were treated at 45° C. with 243 mg (1.60 mmol) of 3,4-dimethoxytoluene in 1 ml of ethanol. 0.180 mmol of a mediator (Table 1) was added with stirring. After approx. 10 minutes, the mixture was treated with 5 ml of an aqueous solution of 2 mg/ml laccase from Trametes versicolor (specific activity: approx. 18 IU/mg, defined with ABTS as substrate). After a reaction time of 22 hours with exposure to air, the reaction solution was extracted with chloroform and examined by N spectroscopy and gas chromatography. Yields of 3,4-dimethoxybenzaldehyde and 3,4-dimethoxybenzyl alcohol, see Table 1.

Aufarbeitung

  1. additiondiluting to 1/4)
  2. addition0.180 mmol of a mediator (Table 1) was added
  3. extractionAfter a reaction time of 22 hours with exposure to air, the reaction solution was extracted with chloroform

Quellen und Nachweise

ORD-Eintrag
ord-15dd6d7afc2847339f67aa9bf42f1109
Quelldatensatz
uspto-grants-2000_02
Patentnummer
US06023000

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