Hydrochloric Acid → Carbonic acid, 2-methoxy-4-methylphenyl methyl ester

HRID 240238

Reaktionsgleichung

Reaktionsgleichung von HRID 240238
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[CH:5][C:4]=1[OH:10].N1C=CC=CC=1.Cl[C:18]([O:20][CH3:21])=[O:19].Cl>ClCCl.CN(C1C=CN=CC=1)C>[C:18](=[O:19])([O:20][CH3:21])[O:10][C:4]1[CH:5]=[CH:6][C:7]([CH3:9])=[CH:8][C:3]=1[O:2][CH3:1]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 6586Methyl chloroformateHCID 71442-Methoxy-4-Methylphenol

Produkt 1

HCID 15636422Carbonic acid, 2-methoxy-4-methylphenyl methyl esterAusbeute 74,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

2-methoxy-4-methylphenol (250 mmol) was dissolved in dry dichoromethane (500 ml) with pyridine (392 mmol) and DMAP (N,N-dimethyl-4-aminopyridine, 4.26 mmol). Methyl chloroformate (317 mmol) was added slowly to this solution and the reaction was stirred at room temperature for 3 hours. The reaction mixture was then poured onto a 2M HCl solution (120 ml), and the aqueous layer was extracted twice with dichloromethane (50 ml). Then the combined organic layers were washed twice with water (100 ml), dried over MgSO4 and filtered. The solvent was evaporated and the residue distilled under reduced pressure (120-140° C., 0.4 mbar) to give 38 g (186 mmol, 74% yield) of pure 2-methoxy-4-methyl-phenyl methyl carbonate.

Aufarbeitung

  1. extractionthe aqueous layer was extracted twice with dichloromethane (50 ml)
  2. washThen the combined organic layers were washed twice with water (100 ml)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customThe solvent was evaporated
  6. distillationthe residue distilled under reduced pressure (120-140° C., 0.4 mbar)

Quellen und Nachweise

ORD-Eintrag
ord-0f4f5e64b9c84451b283c4560e92bbb4
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08648033B2

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