Formaldehyde → 3-t-butyl-5-methoxysalicylaldehyde

HRID 1062517

Reaktionsgleichung

Reaktionsgleichung von HRID 1062517
C([Mg]Br)C.[C:5]([C:9]1[CH:14]=[C:13]([O:15][CH3:16])[CH:12]=[CH:11][C:10]=1[OH:17])([CH3:8])([CH3:7])[CH3:6].[CH2:18]=[O:19].C(N(CC)CC)C>C1COCC1.C1(C)C=CC=CC=1.CCOCC>[C:5]([C:9]1[CH:14]=[C:13]([O:15][CH3:16])[CH:12]=[C:11]([CH:18]=[O:19])[C:10]=1[OH:17])([CH3:8])([CH3:6])[CH3:7]

Komponenten

8

Edukt 4

HCID 712FormaldehydeHCID 8456Butylated HydroxyanisoleHCID 8471TriethylamineHCID 178418443HCID 178418443, Verbindung

Produkt 1

HCID 102624643-t-butyl-5-methoxysalicylaldehydeAusbeute 56 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 1140TolueneLösungsmittelHCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Into a 1 liter reactor thoroughly dried and purged with argon, 36.6 ml of an ether solution containing 110 mmol of ethylmagnesium bromide and 73.4 ml of ether were introduced. To the reactor, a solution containing 18.39 g (100 mmol) of 2-tert-butyl-4-methoxyphenol diluted with 90 ml of a THF was dropwise added at 0° C. over a period of 30 minutes, then the temperature of the system was slowly raised to room temperature, and the reaction solution was stirred at room temperature for 1 hour. Then, 350 ml of toluene was added, and the system was heated to 100° C. to distill off about 180 ml of a mixed solution of ether and THF, whereby an opaque white slurry was obtained. After the slurry was cooled to 50° C., 4.50 g (150 mmol) of paraformaldehyde and 21.0 ml (150 mmol) of triethylamine were added, followed by stirring at 80 to 90° C. for 1.5 hours. The reaction solution was allowed to cool to room temperature and then quenched with 10% hydrochloric acid. The organic layer was concentrated, and the solid precipitated was vacuum dried to obtain 11.66 g (yield: 56%) of 3-t-butyl-5-methoxysalicylaldehyde.

Aufarbeitung

  1. customInto a 1 liter reactor thoroughly dried
  2. custompurged with argon, 36.6 ml of an ether solution
  3. additionwere introduced
  4. additionwas dropwise added at 0° C. over a period of 30 minutes
  5. temperaturethe system was heated to 100° C.
  6. distillationto distill off about 180 ml of a mixed solution of ether and THF, whereby an opaque white slurry
  7. customwas obtained
  8. temperatureAfter the slurry was cooled to 50° C.
  9. stirringby stirring at 80 to 90° C. for 1.5 hours
  10. temperatureto cool to room temperature
  11. customquenched with 10% hydrochloric acid
  12. concentrationThe organic layer was concentrated
  13. customthe solid precipitated
  14. customdried

Quellen und Nachweise

ORD-Eintrag
ord-3db57c9113e94c208ede5a7ad4a43984
Quelldatensatz
uspto-grants-2005_11
Patentnummer
US06962890B2

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