Hydrochloric Acid → 2-Hydroxy-5-nitrobenzyl alcohol

HRID 32322

Reaktionsgleichung

Reaktionsgleichung von HRID 32322
[OH:1][C:2]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:3]=1[CH:4]=[O:5].[BH4-].[Na+].Cl>[OH-].[Na+].CO>[OH:5][CH2:4][C:3]1[CH:6]=[C:7]([N+:10]([O-:12])=[O:11])[CH:8]=[CH:9][C:2]=1[OH:1]

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 668085-NitrosalicylaldehydeHCID 4311764Sodium borohydride

Produkt 1

HCID 27638232-Hydroxy-5-nitrobenzyl alcoholAusbeute 100,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittel2×HCID 14798Sodium HydroxideLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of 2-hydroxy-5-nitrobenzaldehyde (5.01 g, 30 mmol) in a mixture of 60 mL 1M NaOH and 30 mL MeOH was cooled to 0° C. NaBH4 (1.13 g, 30 mmol) solution in 15 ml 1M NaOH and 5 mL MeOH was added slowly. The reaction mixture was stirred for 24 hours at room temperature. The mixture was poured into ice cooled 2M HCl and extracted with EtOAc. The organic layer was washed, dried, and evaporated in vacuo to give the alcohol as a yellow solid (5.1 g, 100%): MP 112-114° C.; 1H NMR (DMSO-d6, 400 MHz) δ 11.08 (s, 1H), 8.18 (d, 1H, J=2.5 Hz), 8.00 (dd, 1H, J=2.5 and 8.7 Hz), 6.92 (d, 1H, J=8.8 Hz), 5.20 (br, 1H), 4.49 (s, 2H).

Aufarbeitung

  1. additionThe mixture was poured into ice
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed
  4. customdried
  5. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-c8e42d1df607468b897faae336df3317
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07427608B2

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