Chloromethyl Methyl Ether → HCID 88220868, Verbindung

HRID 581021

Reaktionsgleichung

Reaktionsgleichung von HRID 581021
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][S:9][C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.[H-].[Na+].Cl[CH2:20][O:21][CH3:22].[Cl-].[Na+].O.[C:26]([O:29][CH2:30]C)(=O)C>CN(C)C=O>[CH3:20][O:21][CH2:22][O:16][C:13]1[CH:14]=[CH:15][C:10]([S:9][S:8][C:5]2[CH:4]=[CH:3][C:2]([O:1][CH2:26][O:29][CH3:30])=[CH:7][CH:6]=2)=[CH:11][CH:12]=1

Komponenten

6

Edukt 4

HCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 2806654-[(4-Hydroxyphenyl)disulfanyl]phenolHCID 131718255Brine ethyl acetate

Produkt 1

HCID 88220868HCID 88220868, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 4-hydroxyphenyldisulfide (650 mg, 2.60 mmol) in 10 mL of anhydrous N,N-dimethylformamide at 10° C. was added sodium hydride (230 mg, 5.75 mmol, 60% dispersion in mineral oil). After stirring for 15 minutes, chloromethylmethyl ether (0.44 mL, 5.75 mmol) was added via syringe. The reaction was warmed to ambient temperature and stirred for 0.5 hours. The mixture was distributed between brine/ethyl acetate (20 mL each). The layers were separated and the aqueous phase extracted with ethyl acetate (2×20 mL). The organic was dried (sodium sulfate) and concentrated to a yellow oil (993 mg, 100%). An analytical sample of 4-(methoxymethyloxy)-phenyldisulfide was prepared by chromatography (silicon dioxide, 4% ethyl acetate/hexanes). 1H NMR (DMSO-d6) d 7.40 (d, J=6.9 Hz, 4H), 7.00 (d, J=6.9 Hz, 4H), 5.15 (s, 4H), 3.32 (s, 6H). FD mass spec: 338. Anal. Calcd. for C16H18O4S2 : C, 56.78; H, 5.36. Found: C, 57.08; H, 5.44.

Aufarbeitung

  1. stirringstirred for 0.5 hours
  2. customThe layers were separated
  3. extractionthe aqueous phase extracted with ethyl acetate (2×20 mL)
  4. dry with materialThe organic was dried (sodium sulfate)
  5. concentrationconcentrated to a yellow oil (993 mg, 100%)

Quellen und Nachweise

ORD-Eintrag
ord-adcca7a3ec7e4e9d9b0cea250ce2a757
Quelldatensatz
uspto-grants-1999_07
Patentnummer
US05919800

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