Pyridine → Methyl 6-formyl-2-naphthalenecarboxylate

HRID 463035

Reaktionsgleichung

Reaktionsgleichung von HRID 463035
N1C=CC=CC=1.[OH:7][CH2:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[CH:15]=[C:14]([C:19]([O:21][CH3:22])=[O:20])[CH:13]=[CH:12]2>C(Cl)Cl>[C:19]([C:14]1[CH:15]=[C:16]2[C:11](=[CH:12][CH:13]=1)[CH:10]=[C:9]([CH:8]=[O:7])[CH:18]=[CH:17]2)([O:21][CH3:22])=[O:20]

Komponenten

4

Edukt 2

HCID 1049PyridineHCID 11127663Methyl 6-(Hydroxymethyl)-2-naphthoate

Produkt 1

HCID 11521354Methyl 6-formyl-2-naphthalenecarboxylateAusbeute 96,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A mixture of 5 mL (61.8 mmol) of pyridine and 70 mL of CH2Cl2 was cooled to 0° C. Then 3.0 g (30 mmol) of CrO3 was added in several portions. The mixture was stirred at 0° C. for 15 min before a solution of 0.69 g (3.19 mmol) of methyl 6-hydroxymethyl-2-naphthoate in 10 mL of CH2Cl2 was added. The mixture was stirred at room temperature for 2 hr and then filtered through Florisil (500 mL CH2Cl2 rinse). The filtrate and washings were concentrated and filtered through 50 g of silica gel with 50% EtOAc/hexane to give 0.66 g (96% yield) of the pure aldehyde as a white solid. The analytical sample was recrystallized from EtOAc/hexane: mp 132°-134° C.; IR (mull) 1740, 1700, 1350, 1310, 1270, 1220, 1180, 1140, 1110, 990, 920, 830, 780, 760 cm- 1 ; 1H NMR (CDCl3) δ4.00 (s, 3, CO2CH3), 8.0-8.7 (m, 6, ArH), 10.23 (s, 1, CHO); MS calcd for C13H10O3 214.0630, found 214.0627.

Aufarbeitung

  1. additionwas added
  2. filtrationfiltered through Florisil (500 mL CH2Cl2 rinse)
  3. concentrationThe filtrate and washings were concentrated
  4. filtrationfiltered through 50 g of silica gel with 50% EtOAc/hexane

Quellen und Nachweise

ORD-Eintrag
ord-8cbf1c98b30946b7871485e9ae7f2b92
Quelldatensatz
uspto-grants-1985_05
Patentnummer
US04518609

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