Reaktion #582300

ord-7dcb54eaf9724e129d27e1c0e1ceddf5

Reaktionsgleichung

CC1(C)Cc2ccccc2C1=O
dimethylindanone
CCNCC
Diethylamine
O=S(=O)(O)O
H2SO4
C=O
formaldehyde
→
C=C1C(=O)c2ccccc2C1(C)C
product
Ausbeute 15.9%
C=C1C(=O)c2ccccc2C1(C)C
3,3-Dimethyl-2-methylene-indan-1-one
Ausbeute 15.9%

Edukte

CC1(C)Cc2ccccc2C1=O
dimethylindanone
CCNCC
Diethylamine
O=S(=O)(O)O
H2SO4
C=O
formaldehyde

Reagenzien

Keine

Reaktionsbedingungen

Temperatur
110°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeAqueous workup yielded
  2. 2
    workup.ADDITIONa ca. 1:1 mixture of starting material and product which
  3. 3
    Sonstigewas separated by FC on SiO2

Vorschrift

Diethylamine (8.76 g, 0.12 mol) was cooled to 0° C. and 62.5% aq. H2SO4 was added slowly. Aqueous formaldehyde solution (36.5%, 9.86 g, 0.12 mol) was added, followed by dimethylindanone (16.0 g, 0.10 mol). The mixture was heated to 110° C. for 5.5 h. Aqueous workup yielded a ca. 1:1 mixture of starting material and product which was separated by FC on SiO2 to yield the product as a colourless oil (2.73 g, 13%).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07538243B2uspto-grants-2009_05