Methyl Ethyl Ketone → 4-(Bicyclo[2.2.1]hept-5-en-2-yl)-3-methylbut-3-en-2-one

HRID 267453

Reaktionsgleichung

Reaktionsgleichung von HRID 267453
[CH3:1][C:2](=[O:5])[CH2:3][CH3:4].[CH:6]12[CH2:12][CH:9]([CH:10]=[CH:11]1)[CH2:8][CH:7]2[CH:13]=O.[OH-].[Na+].C1(C)C(S(O)(=O)=O)=CC=CC=1>O>[CH:9]12[CH2:12][CH:6]([CH:7]([CH:13]=[C:3]([CH3:4])[C:2](=[O:5])[CH3:1])[CH2:8]1)[CH:11]=[CH:10]2

Komponenten

6

Edukt 4

HCID 6569Methyl Ethyl KetoneHCID 69252-Methylbenzenesulfonic acidHCID 14798Sodium HydroxideHCID 95117Bicyclo(2.2.1)hept-5-ene-2-carboxaldehyde

Produkt 1

HCID 534266304-(Bicyclo[2.2.1]hept-5-en-2-yl)-3-methylbut-3-en-2-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A mixture of 80 ml. of 2-butanone (1.1 moles), 61.1 grams (0.5 moles) of 5-norbornene-2-carboxaldehyde, and 250 ml. of water containing 6 ml. of 40% sodium hydroxide solution was stirred rapidly at 50°C. for 2 hours when most of the aldehyde had been consumed (as determined by infrared analysis) and an aldol had formed. Stirring was continued and the temperature was slowly raised to 70°C. and kept there for 30 minutes causing dehydration of 75% of the aldol. A small amount of toluene sulfonic acid was added which catalyzed the dehydration of the remaining aldol. 90.8 grams of crude material which was a viscous liquid was distilled through a short Vigreux-column to give 4-(5-norbornenyl)-3-methyl-but-3-en-2-one which had a boiling point of 121°-122°C. at 10 mm., nD 25 = 1.5156.

Aufarbeitung

  1. additionA mixture of 80 ml
  2. customhad been consumed (as determined by infrared analysis)
  3. customan aldol had formed
  4. distillationwas distilled through a short Vigreux-column

Quellen und Nachweise

ORD-Eintrag
ord-fba4d26a886d4770931bd9a9fc81c0b3
Quelldatensatz
uspto-grants-1976_03
Patentnummer
US03942761

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