Formaldehyde → 1208091-01-3

HRID 1014385Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1014385
[CH3:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[NH2:10].[CH2:11]=O.C[O-].[Na+].[BH4-].[Na+]>CO.C(OCC)(=O)C>[CH3:11][NH:10][C:3]1[CH:4]=[CH:5][C:6]([O:8][CH3:9])=[CH:7][C:2]=1[CH3:1]

Komponenten

7

Edukt 4

HCID 712FormaldehydeHCID 76102-Methyl-4-methoxyanilineHCID 4311764Sodium borohydrideHCID 10942334Sodium Methoxide

Produkt 1

HCID 145678141208091-01-3Ausbeute 91,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A suspension of [2-methyl-4-(methyloxy)phenyl]amine (5 ml, 39.2 mmol), paraformaldehyde (5.88 g, 196 mmol), and sodium methoxide (10.58 g, 196 mmol) in methanol (100 ml) was maintained at 50° C. for 5 hours, cooled, and sodium borohydride (7.41 g, 196 mmol) was added portionwise. The resulting suspension was re-heated to 50° C. and maintained for 16 hours. The reaction was cooled, poured into ethyl acetate/saturated sodium bicarbonate, and the organic layer was dried over sodium sulfate, filtered, taken to a residue under reduced pressure, and purified by column chromatography to afford N,2-dimethyl-4-(methyloxy)aniline (5.40 g, 35.7 mmol, 91% yield) as a pale orange oil. 1H NMR (400 MHz, DMSO-d6) δ ppm 6.55-6.68 (m, 2 H), 6.34-6.40 (m, 1 H), 4.47-4.66 (m, 1 H), 3.62 (s, 3 H), 2.66 (d, J=5.0 Hz, 3 H), 2.04 (s, 3 H).

Aufarbeitung

  1. temperaturecooled
  2. temperatureThe resulting suspension was re-heated to 50° C.
  3. temperaturemaintained for 16 hours
  4. temperatureThe reaction was cooled
  5. dry with materialthe organic layer was dried over sodium sulfate
  6. filtrationfiltered
  7. custompurified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-8092586925c54cfb88c9bd4dbcf0fc53
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07981903B2

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