Dimethyl Sulfoxide → 2-Heptyloxy-4-iodobenzaldehyde

HRID 1171432

Reaktionsgleichung

Reaktionsgleichung von HRID 1171432
CS(C)=O.C(Cl)(=O)C(Cl)=O.[CH2:11]([O:18][C:19]1[CH:24]=[C:23]([I:25])[CH:22]=[CH:21][C:20]=1[CH2:26][OH:27])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17].C(N(CC)CC)C>ClCCl.O>[CH2:11]([O:18][C:19]1[CH:24]=[C:23]([I:25])[CH:22]=[CH:21][C:20]=1[CH:26]=[O:27])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]

Komponenten

7

Edukt 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 68768142(2-Heptyloxy-4-iodophenyl)methanol

Produkt 1

HCID 860544942-Heptyloxy-4-iodobenzaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel3×

Versuchsvorschrift

A solution of dimethyl sulfoxide (DMSO) (41.4 mmol, 3 ml) in dichloromethane (10 ml) is added to a solution of 1.8 ml of oxalyl chloride (20.7 mmol) in 55 ml of dichloromethane, dropwise, at −78° C. After stirring for 15 minutes, a solution of (2-heptyloxy-4-iodophenyl)methanol obtained in Step b (6.55 g, 18.8 mmol) in 25 ml of dichloromethane is added dropwise. After stirring for 20 minutes, 14 ml of triethylamine are added. After stirring for 2 hours, the reaction medium is hydrolysed by addition of water. The desired product is extracted by addition of ethyl acetate. The organic phase is washed with water, dried with magnesium sulfate and concentrated using a rotary evaporator. After evaporation of the solvents, 6.49 g (100%) of the expected compound are recovered in the form of a yellow solid.

Aufarbeitung

  1. customat −78° C
  2. stirringAfter stirring for 20 minutes
  3. stirringAfter stirring for 2 hours
  4. extractionThe desired product is extracted by addition of ethyl acetate
  5. washThe organic phase is washed with water
  6. dry with materialdried with magnesium sulfate
  7. concentrationconcentrated
  8. customa rotary evaporator
  9. customAfter evaporation of the solvents, 6.49 g (100%) of the expected compound
  10. customare recovered in the form of a yellow solid

Quellen und Nachweise

ORD-Eintrag
ord-98427741d4fd48dd8ff517848ac386b8
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07829588B2

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