Formaldehyde → 4-Hydroxybutyraldehyde 2-hydroxytetrahydrofuran

HRID 1638443

Reaktionsgleichung

Reaktionsgleichung von HRID 1638443
O1C=CCC1.OS(O)(=O)=O.[OH-].[Na+].[OH:13][CH2:14][CH2:15][CH2:16][CH:17]=[O:18].[OH:19][CH:20]1[CH2:24][CH2:23][CH2:22][O:21]1.C=O.[H][H].C(O)CCCO.CC(CCO)CO>[Ni].O>[OH:18][CH2:17][CH2:16][CH2:15][CH:14]=[O:13].[OH:19][CH:20]1[CH2:24][CH2:23][CH2:22][O:21]1

Komponenten

12

Edukt 9

HCID 712FormaldehydeHCID 1118Sulfuric AcidHCID 80641,4-ButanediolHCID 14798Sodium Hydroxide2×HCID 180532-Methyl-1,4-butanediolHCID 709342,3-DihydrofuranHCID 93002Tetrahydro-2-hydroxyfuranHCID 930934-HydroxybutanalHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 867434974-Hydroxybutyraldehyde 2-hydroxytetrahydrofuran

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 935NickelKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

The 4-hydroxybutyraldehyde/2-hydroxytetrahydrofuran was prepared by adding 20 parts of 2,3-dihydrofuran to 10 parts of 2% H2SO4 over about 20 minutes, keeping the temperature at 35° with cooling. The mixture was then neutralized with 30% NaOH. The organic portion of the resulting homogeneous product was a 2:1 mixture of 4-hydroxybutyraldehyde and its cyclic hemiacetal, 2-hydroxytetrahydrofuran. Thirty parts of that mixture were mixed with 10 parts of water, 4.3 parts of 37% aqueous formaldehyde, 0.53 parts of 30% NaOH, and 2 parts of Raney nickel. Hydrogenation was then carried out at 27,576 kPa (gauge) hydrogen at 150° for 2 hours in a shaker tube. The organic portion of the resulting product consisted mainly of 1,4-butanediol and 2-methyl-1,4-butanediol, in a ratio of 55:45. There were also some unidentified higher boilers.

Aufarbeitung

  1. customat 35°
  2. temperaturewith cooling

Quellen und Nachweise

ORD-Eintrag
ord-adb34929297e49359d06c1c1b69d311e
Quelldatensatz
uspto-grants-1989_11
Patentnummer
US04879420

Verknüpfte Notizen

Wird geladen…