Diethyl Ether → 2-Methyl-1-naphthalenol methylcarbonate

HRID 1003120Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1003120
C(N(CC)CC)C.[CH3:8][C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]=1[OH:19].Cl[C:21]([O:23][CH3:24])=[O:22].C([O:27]CC)C>C(OCC)(=O)C>[CH3:8][C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]=1[OH:19].[CH3:24][O:23][C:21](=[O:27])[O-:22]

Komponenten

6

Edukt 4

HCID 3283Diethyl EtherHCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 240552-Methyl-1-naphthol

Produkt 1

HCID 187952202-Methyl-1-naphthalenol methylcarbonateAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

2.64 g (26 mmole) of triethylamine were added to a stirred solution of 3.16 g (20 mmole) of 2-methyl-1-naphthol in 25 mL of ethyl acetate, while the solution was maintained in an ice bath. Then 2.36 g (25 mmole) methyl chloroformate were added portionwise to the solution. The reaction mixture was stirred for one hour and then 100 mL diethylether was added. The reaction mixture was filtered over a Celite pad and the filtrate concentrated to give 3.65 g (85% yield) of an oil which was crystallized in hexane. The resulting crystals had a melting point of 54-55° C. The following 1HNMR was obtained: (300 MHz, DMSO-d6) δ2.30 (s, 3H), 3.89 (s, 3H), 7.44 (d, 1H, J=8 Hz), 7.48-7.58 (m, 2H), 7.78 (t, 2H, J=9 Hz), 7.95 (d, 1H, J=8 Hz). The mass spectrum showed a molecular ion at m/z 216.

Aufarbeitung

  1. temperaturewas maintained in an ice bath
  2. filtrationThe reaction mixture was filtered over a Celite pad
  3. concentrationthe filtrate concentrated

Quellen und Nachweise

ORD-Eintrag
ord-4e1b279eb5d645c3a8be1dcc8597531e
Quelldatensatz
uspto-grants-2000_04
Patentnummer
US06045590

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