Chloromethyl Methyl Ether → 3-Benzyloxy-4-methoxybenzaldehyde

HRID 652800

Reaktionsgleichung

Reaktionsgleichung von HRID 652800
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][C:16]=1[OH:17])[CH:12]=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH3:20]OCCl>CN(C)C=O.O>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][C:16]=1[O:17][CH3:20])[CH:12]=[O:13])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 3

HCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydride2×HCID 110206353-Benzyloxy-4-hydroxybenzaldehyde

Produkt 1

HCID 806713-Benzyloxy-4-methoxybenzaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

A solution of 300 g of 3-benzyloxy-4-hydroxybenzaldeyde (obtained as described in example 62) in 600 ml of dimethylformamide was added to a suspension of 34.6 g of sodium hydride in 346 ml of dimethylformamide under stirring in nitrogen atmosphere. After complete dissolution of sodium hydride 116 g of chloromethyl methyl ether were added; stirring was continued for 30 minutes. The mixture was then diluted with water and extracted with ethyl ether. The combined organic phase was dried over sodium sulfate, filtered and evaporated. The residue was distilled (b.p. 178°-183° C./0.1 mm Hg) to give 3-benzyloxy-4-methoxybenzaldehyde, m.p. 30° C. (from petroleum ether, b.p. 30°-70° C.).

Aufarbeitung

  1. additionwere added
  2. stirringstirring
  3. extractionextracted with ethyl ether
  4. dry with materialThe combined organic phase was dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. distillationThe residue was distilled (b.p. 178°-183° C./0.1 mm Hg)

Quellen und Nachweise

ORD-Eintrag
ord-95efb3875a0543a7a9361ee7cf4d6162
Quelldatensatz
uspto-grants-1987_06
Patentnummer
US04673671

Verknüpfte Notizen

Wird geladen…