Methylparaben → Methyl 4-(allyloxy)benzoate

HRID 34731

Reaktionsgleichung

Reaktionsgleichung von HRID 34731
[H-].[Na+].[CH3:3][CH2:4][CH2:5]CCC.[OH:9][C:10]1[CH:19]=[CH:18][C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][CH:11]=1.C(Br)C=C>CCOCC.O.CN(C=O)C>[CH2:5]([O:9][C:10]1[CH:11]=[CH:12][C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:18][CH:19]=1)[CH:4]=[CH2:3]

Komponenten

8

Edukt 4

HCID 7456MethylparabenHCID 7841Allyl bromideHCID 8058HexaneHCID 24758Sodium hydride

Produkt 1

HCID 4645407Methyl 4-(allyloxy)benzoate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

NaH (60% in oil, 10 g., 0.25 mol) was washed 3×100 ml. hexane in place. 350 ml. DMF was then added, the mixture stirred under N2, and methyl 4-hydroxybenzoate (38.0 g., 0.25 mol) added portionwise over 20 minutes as H2 evolved. Allyl bromide (21.6 ml., 0.25 mol) was then added via syringe over 5 minutes. After 40 minutes additional stirring, the reaction mixture was poured into 400 ml. ice and water and 150 ml. ether was added. The layers were separated and the aqueous layer extracted 4×150 ml. fresh ether and 1×100 ml. hexane. The organic layers were combined, washed 2×150 ml. saturated NaHCO3, dried over MgSO4, and stripped to yield title product, 47.6 g., 3.89 (s, 3H), 4.60 (m, 2H), 5.46 (m, 2H), 6.1 (m, 1H), 6.99 (d, 2 H), 8.10 (d, 2H).

Aufarbeitung

  1. additionthe reaction mixture was poured into 400 ml
  2. customThe layers were separated
  3. extractionthe aqueous layer extracted 4×150 ml
  4. washwashed 2×150 ml
  5. dry with materialsaturated NaHCO3, dried over MgSO4

Quellen und Nachweise

ORD-Eintrag
ord-884ac44b2889485ba15961c33b4cdcbb
Quelldatensatz
uspto-grants-1988_08
Patentnummer
US04762921

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