Dimethyl Sulfoxide → (+/-)-6-Benzyloxy-2-methoxy-2,5,7,8-tetramethylchroman

HRID 268423

Reaktionsgleichung

Reaktionsgleichung von HRID 268423
[OH:1][C:2]1[C:3]([CH3:17])=[C:4]2[C:9](=[C:10]([CH3:13])[C:11]=1[CH3:12])[O:8][C:7]([O:15][CH3:16])([CH3:14])[CH2:6][CH2:5]2.C(=O)([O-])[O-].[K+].[K+].CS(C)=O.[CH2:28](Cl)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>O>[CH2:28]([O:1][C:2]1[C:3]([CH3:17])=[C:4]2[C:9](=[C:10]([CH3:13])[C:11]=1[CH3:12])[O:8][C:7]([O:15][CH3:16])([CH3:14])[CH2:6][CH2:5]2)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Komponenten

6

Edukt 4

HCID 679Dimethyl SulfoxideHCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 1037632H-1-Benzopyran-6-ol, 3,4-dihydro-2-methoxy-2,5,7,8-tetramethyl-

Produkt 1

HCID 14415660(+/-)-6-Benzyloxy-2-methoxy-2,5,7,8-tetramethylchroman

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 70.8 g. of (±)-6-hydroxy-2-methoxy-2,5,7,8-tetramethylchroman, 90.9 g. of anhydrous potassium carbonate, 300 ml. of dimethylsulfoxide and 69 ml. of benzyl chloride was stirred at 23° under N2 for 24 hours. The suspension was poured into water and extracted with ether. The ether solutions were washed with brine, dried over sodium sulfate and stripped of solvent to give (±)-6-benzyloxy-2-methoxy-2,5,7,8-tetramethylchroman as an oil which solidified to a light yellow mass, m.p. 70°-72.5°.

Aufarbeitung

  1. additionA mixture of 70.8 g
  2. extractionextracted with ether
  3. washThe ether solutions were washed with brine
  4. dry with materialdried over sodium sulfate

Quellen und Nachweise

ORD-Eintrag
ord-6f8275b7ff9d4d8f90f989ea0ff322cf
Quelldatensatz
uspto-grants-1976_03
Patentnummer
US03947473

Verknüpfte Notizen

Wird geladen…