2,5-Dimethylphenol → 4-Chloro-2,5-xylenol

HRID 2297079

Reaktionsgleichung

Reaktionsgleichung von HRID 2297079
[C:1]1([OH:9])[C:2]([CH3:8])=[CH:3][CH:4]=[C:5]([CH3:7])[CH:6]=1.S(Cl)([Cl:13])(=O)=O.S(=O)(O)[O-].[Na+]>ClCCl.C1(SC2C=CC=CC=2)C=CC=CC=1>[Cl:13][C:4]1[CH:3]=[C:2]([CH3:8])[C:1]([OH:9])=[CH:6][C:5]=1[CH3:7]

Komponenten

6

Edukt 3

HCID 72672,5-DimethylphenolHCID 24648Sulfuryl chlorideHCID 23665763Sodium Bisulfite

Produkt 1

HCID 707564-Chloro-2,5-xylenolAusbeute 97,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8766Diphenyl sulfideKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
10 °C

Versuchsvorschrift

To a solution of 100 g (0.82 mol) of 2,5-xylenol and 0.9 g of diphenyl sulfide in 700 mL of dichloromethane was added a solution of 106 g (0.79 mol) of sulfuryl chloride in 100 mL of dichloromethane, maintaining the temperature at 5-15° C. The mixture was stirred for an additional hour and then poured onto 400 g of ice-water containing 5 g of sodium bisulfite. The layers were separated, and the organic phase was washed with water, dried (MgSO4), and concentrated to dryness. The crude solids were slurried with a minimum amount of hexanes, filtered, and suction-dried to give 121 g (94%) of product, homogeneous by Thin Layer Chromatography (TLC), GC, and 1H-NMR analysis. 1H-NMR (CDCl3) δ 2.18 (s, 3H), 2.27 (s, 3H), 4.61 (s, 1H), 6.63 (s, 1H), 7.07 (s, 1H). Lit (Blackstock, Aust. J. Chem. 1973, 26, 775): mp 74-75° C.

Aufarbeitung

  1. customThe layers were separated
  2. washthe organic phase was washed with water
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated to dryness
  5. filtrationfiltered
  6. customsuction-dried

Quellen und Nachweise

ORD-Eintrag
ord-1aa87337794c4356abec21a45ce0ad11
Quelldatensatz
uspto-grants-2002_12
Patentnummer
US06489517B1

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