Isophthalaldehyde → 3-(Hydroxymethyl)benzaldehyde

HRID 22601

Reaktionsgleichung

Reaktionsgleichung von HRID 22601
[CH:1](=[O:10])[C:2]1[CH:9]=[CH:8][CH:7]=[C:4]([CH:5]=[O:6])[CH:3]=1.[BH4-].[Na+]>C(O)C>[OH:10][CH2:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6]

Komponenten

4

Edukt 2

HCID 34777IsophthalaldehydeHCID 4311764Sodium borohydride

Produkt 1

HCID 131314553-(Hydroxymethyl)benzaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of isophtalaldehyde (8 g) in ethanol (80 mL) at room temperature was added NaBH4 portion wise, until about 50% reaction by TLC. The reaction mixture was quenched with 25% ammonium acetate, extracted with ethyl acetate, which was washed with brine (2×), dried over sodium sulfate, filtered and evaporated to dryness. Purification of the residue by flash chromatography using 50% ether in hexane afforded the pure title compound.

Aufarbeitung

  1. customuntil about 50% reaction by TLC
  2. customThe reaction mixture was quenched with 25% ammonium acetate
  3. extractionextracted with ethyl acetate, which
  4. washwas washed with brine (2×)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated to dryness
  8. customPurification of the residue by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-d1cdac45a5fa47929f66e1f76c7ac649
Quelldatensatz
uspto-grants-1995_06
Patentnummer
US05428171

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