Formaldehyde → 1-Diethylamino-5-methyl-6-(m-methoxyphenyl)hex-2-yne

HRID 1077127Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1077127
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][CH:10]([CH3:14])[CH2:11][C:12]#[CH:13])[CH:6]=[CH:7][CH:8]=1.O1[CH2:20][CH2:19]COO1.C=O.[CH2:23]([NH:25][CH2:26]C)[CH3:24].[OH-].[Na+]>O1CCOCC1.C(O)(=O)C>[CH2:23]([N:25]([CH2:19][CH3:20])[CH2:26][C:13]#[C:12][CH2:11][CH:10]([CH3:14])[CH2:9][C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=1)[CH3:24]

Komponenten

8

Edukt 5

HCID 712FormaldehydeHCID 8021DiethylamineHCID 14798Sodium HydroxideHCID 19593658CID 19593658HCID 214857465-(m-Methoxyphenyl)-4-methyl-pent-1-yne

Produkt 1

HCID 214854231-Diethylamino-5-methyl-6-(m-methoxyphenyl)hex-2-yne

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

Heat 5-(m-methoxyphenyl)-4-methyl-pent-1-yne (8 g), trioxan (0.5 g), 30% formalin (5.5 cc), diethylamine (4 g), acetic acid (2.75 g), dioxan (25 cc) and cuprous chloride (0.12 g) together at 70° for 15 hours. Make cooled solution alkaline with 10% aqueous sodium hydroxide and extract with ether. Wash the ethereal solution with water and extract with 10% hydrochloric acid (3 × 20 cc). Combine the acid extracts, wash with ether and make alkaline with 10% aqueous sodium hydroxide and extract with ether. Wash the ethereal solution, dry, remove the solvent and distil the residue at 0.1 mm to obtain 1-diethylamino-5-methyl-6-(m-methoxyphenyl)-hex-2-yne.

Aufarbeitung

  1. extractionextract with ether
  2. washWash the ethereal solution with water
  3. extractionextract with 10% hydrochloric acid (3 × 20 cc)
  4. washCombine the acid extracts, wash with ether
  5. extractionextract with ether
  6. washWash the ethereal solution
  7. customdry
  8. customremove the solvent
  9. customdistil the residue at 0.1 mm

Quellen und Nachweise

ORD-Eintrag
ord-34a146ef3e4c4260bbfcf3faf9846c68
Quelldatensatz
uspto-grants-1976_05
Patentnummer
US03959322

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