Water → Dimethyl (m-phenylbenzyl)malonate

HRID 893369

Reaktionsgleichung

Reaktionsgleichung von HRID 893369
[C:1]([O:8][CH3:9])(=[O:7])[CH2:2][C:3]([O:5][CH3:6])=[O:4].[C:10]1([C:16]2[CH:17]=[C:18]([CH:21]=[CH:22][CH:23]=2)[CH2:19]Br)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C[O-].[Na+].O>CO>[C:10]1([C:16]2[CH:17]=[C:18]([CH:21]=[CH:22][CH:23]=2)[CH2:19][CH:2]([C:1]([O:8][CH3:9])=[O:7])[C:3]([O:5][CH3:6])=[O:4])[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 7943Dimethyl malonateHCID 38644053-(Bromomethyl)biphenylHCID 10942334Sodium Methoxide

Produkt 1

HCID 21275952Dimethyl (m-phenylbenzyl)malonateAusbeute 59,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Versuchsvorschrift

Solutions of dimethyl malonate (1.32 g) in dry methanol (5 ml) and 3-phenylbenzyl bromide (2.47 g) in dry methanol (5 ml, hot solution) were added successively to a stirred solution of sodium methoxide [from sodium (0.23 g) and dry methanol (20 ml)]. The resulting mixture was stirred for 2 hours at room temperature and for 2 hours under reflux, then poured into water and extracted with ether. The extracts were washed with water, dried, concentrated and purified by column chromatography using a 1:1 mixture of dichloromethane and 40°-60° C. petrol as eluant to give dimethyl (m-phenylbenzyl)malonate (1.77 g, 59%) as a yellow oil, lR (film) : 1 755 and 1 740 cm-1.

Aufarbeitung

  1. temperatureunder reflux
  2. extractionextracted with ether
  3. washThe extracts were washed with water
  4. customdried
  5. concentrationconcentrated
  6. custompurified by column chromatography
  7. additiona 1:1 mixture of dichloromethane and 40°-60° C. petrol as eluant

Quellen und Nachweise

ORD-Eintrag
ord-f43ba144ab294bb6b95128db469c737f
Quelldatensatz
uspto-grants-1992_06
Patentnummer
US05124353

Verknüpfte Notizen

Wird geladen…