4-Hydroxybenzaldehyde → 4-(2-Tetrahydro-2H-pyranoxy)benzaldehyde

HRID 495319

Reaktionsgleichung

Reaktionsgleichung von HRID 495319
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[O:10]1[CH:15]=[CH:14][CH2:13][CH2:12][CH2:11]1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>ClCCl>[O:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH:11]1[O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 1264-HydroxybenzaldehydeHCID 80803,4-dihydro-2H-pyranHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)

Produkt 1

HCID 112527364-(2-Tetrahydro-2H-pyranoxy)benzaldehydeAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

4-Hydroxybenzaldehyde (43.4 g, 0.355 mol), dihydropyran (44.4 ml, 0.495 mol), pyridinium p-toluenesulphonate (11.6 g, 0.046 mol, 0.1 mol equiv.) and dichloromethane (300 ml) were stirred for 16 h at room temperature. The mixture was washed with dilute aqueous sodium hydroxide solution (2×300 ml), water (200 ml), brine (300 ml), and finally with water (250 ml), dried over sodium sulphate and evaporated to dryness to leave a dark brown oil(63 g, 87%). This was used without further purification in the following step 1CW02. 1H NMR showed expected signals.

Aufarbeitung

  1. washThe mixture was washed with dilute aqueous sodium hydroxide solution (2×300 ml), water (200 ml), brine (300 ml)
  2. dry with materialfinally with water (250 ml), dried over sodium sulphate
  3. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-a876761294254d60891a607502043b2f
Quelldatensatz
uspto-grants-2005_09
Patentnummer
US06939479B2

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