Hydrochloric Acid → 4-(Decyloxy)benzaldehyde

HRID 1701357

Reaktionsgleichung

Reaktionsgleichung von HRID 1701357
[CH2:1]([O:11][C:12]1[CH:20]=[CH:19][C:15]([C:16](O)=[O:17])=[CH:14][CH:13]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[H-].[Al+3].[Li+].[H-].[H-].[H-].Cl.CCOCC>O1CCCC1>[CH2:1]([O:11][C:12]1[CH:13]=[CH:14][C:15]([CH:16]=[O:17])=[CH:19][CH:20]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 1385274-(Decyloxy)benzoic acidHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 1410684-(Decyloxy)benzaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a mixture of 27.8 g (0.1 mole) of 4-(decyloxy)benzoic acid in 500 ml of tetrahydrofuran cooled to 0° C. is slowly added 16.2 g (0.1 mole) of N,N'-carbonyldiimidazole. The mixture is heated to reflux for 1 hour then cooled to -20° C. To the cooled mixture is added 1.9 g (0.05 mole) of lithium aluminum hydride and stirring is continued at -20° C. for 1 hour. To the reaction mixture is slowly added 100 ml of 5% aqueous hydrochloric acid followed by the addition of ether. The ether layer is separated and washed with 5% aqueous hydrochloric acid, water, and 5% aqueous sodium bicarbonate then dried over sodium sulfate, filtered and evaporated to dryness to give 4-(decyloxy)benzaldehyde.

Aufarbeitung

  1. temperatureThe mixture is heated
  2. temperatureto reflux for 1 hour
  3. temperaturethen cooled to -20° C
  4. customThe ether layer is separated
  5. washwashed with 5% aqueous hydrochloric acid, water, and 5% aqueous sodium bicarbonate
  6. dry with materialthen dried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-f7737dd3ed6d4c75ba3a9bbe8680b03e
Quelldatensatz
uspto-grants-1980_03
Patentnummer
US04192895

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