Hydrazine hydrate (1:1) → 4-(Hydroxymethyl)benzohydrazide

HRID 44228

Reaktionsgleichung

Reaktionsgleichung von HRID 44228
[OH:1][CH2:2][C:3]1[CH:12]=[CH:11][C:6]([C:7](OC)=[O:8])=[CH:5][CH:4]=1.O.[NH2:14][NH2:15]>C(O)C>[OH:1][CH2:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([NH:14][NH2:15])=[O:8])=[CH:5][CH:4]=1

Komponenten

4

Edukt 2

HCID 24654Hydrazine hydrate (1:1)HCID 81325Methyl 4-(hydroxymethyl)benzoate

Produkt 1

HCID 432368204-(Hydroxymethyl)benzohydrazide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of methyl 4-(hydroxymethyl)benzoate (6.6 g, 40 mmol) and hydrazine hydrate (6 mL) in ethanol (30 mL) was stirred at reflux for 20 hours. The reaction mixture was concentrated to half volume through atmospheric pressure distillation. The solid was collected by filtration and washed with cold ethanol (2×10 mL). The filtrate was further concentrated and a second crop was similarly obtained and combined. The 4-(hydroxymethyl)benzohydrazide was obtained as a white solid (6.1 g, 93%). 400 MHz 1H NMR (DMSO-d6) δ: 9.68 (s, 1H), 7.75 (dd, J=6.4, 1.6 Hz, 2H), 7.34 (d, J=8.0 Hz, 2H), 5.25 (t, J=6.0 Hz, 1H), 4.50 (d, J=6.0 Hz, 2H), 4.43 (s, 2H).

Aufarbeitung

  1. temperatureat reflux for 20 hours
  2. concentrationThe reaction mixture was concentrated to half volume through atmospheric pressure distillation
  3. filtrationThe solid was collected by filtration
  4. washwashed with cold ethanol (2×10 mL)
  5. concentrationThe filtrate was further concentrated
  6. customa second crop was similarly obtained

Quellen und Nachweise

ORD-Eintrag
ord-0c0fc23b09684c52baf772134855872e
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541407B2

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