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Hydrochloric Acid → 3-(Hydroxymethyl)-4-methylpent-4-en-2-one

HRID 1834160
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1834160
[CH2:1]=[O:2].[O:3]=[C:4]([CH:6]=[C:7]([CH3:9])[CH3:8])[CH3:5].N12CCCN=C1CCCCC2.Cl>>[CH3:8][C:7]([CH:6]([CH2:1][OH:2])[C:4](=[O:3])[CH3:5])=[CH2:9]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 4

HCID 313Hydrochloric AcidHCID 712Formaldehyde2×HCID 8858Mesityl oxideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

Produkt 1

HCID 141866443-(Hydroxymethyl)-4-methylpent-4-en-2-oneAusbeute 78 %

Versuchsvorschrift

30 g (1 mol) of paraformaldehyde were added to a mixture of 490 g (5 mols) of mesityl oxide and 15.2 g (0.1 mol) of 1,8-diazabicyclo[5.4.0]undec-7-ene over the course of 2 - 3 hours at 30° C. After completion of the addition of formaldehyde, the reaction mixture was stirred for about a further hour, then cooled to 0° C and neutralised with dilute hydrochloric acid. The organic phase was separated off and the aqueous phase was repeatedly extracted with methylene chloride. The combined organic phases were dried with zeolite, filtered off and then freed from methylene chloride. The residue (506 g) was fractionally distilled in a high vacuum at about 0.1 - 1 mm Hg. Thereby, 431 g of mesityl oxide were recovered. As a further fraction, 47 g of crude product of boiling point 45° - 85° C/l mm Hg were obtained. A further fractional distillation of this crude product gave 35.5 g of 2-methyl-3-hydroxymethyl-pent-1-en-4-one of boiling point 50° - 52° C/0.2 mm Hg (yield: 78%, relative to mesityl oxide converted), in the form of a colourless liquid.

Aufarbeitung

  1. customThe organic phase was separated off
  2. extractionthe aqueous phase was repeatedly extracted with methylene chloride
  3. dry with materialThe combined organic phases were dried with zeolite
  4. filtrationfiltered off
  5. distillationThe residue (506 g) was fractionally distilled in a high vacuum at about 0.1 - 1 mm Hg
  6. customThereby, 431 g of mesityl oxide were recovered
  7. customAs a further fraction, 47 g of crude product of boiling point 45° - 85° C/l mm Hg were obtained
  8. distillationA further fractional distillation of this crude product

Quellen und Nachweise

ORD-Eintrag
ord-4967a8562db248d68fb817a1c41fd378
Quelldatensatz
uspto-grants-1978_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04069257

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