Water → 4-(4-Phenylbutoxy)styrene

HRID 1603927Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1603927
[CH2:1]([Li])CCC.[C:6]1([CH2:12][CH2:13][CH2:14][CH2:15][O:16][C:17]2[CH:24]=[CH:23][C:20]([CH:21]=O)=[CH:19][CH:18]=2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.O.C(OCC)C>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O1CCCC1.CCCCCC>[C:6]1([CH2:12][CH2:13][CH2:14][CH2:15][O:16][C:17]2[CH:24]=[CH:23][C:20]([CH:21]=[CH2:1])=[CH:19][CH:18]=2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Komponenten

8

Edukt 4

HCID 962WaterHCID 3283Diethyl EtherHCID 158710154-(4-Phenylbutoxy)benzaldehydeHCID 178418339Butyllithium

Produkt 1

HCID 196062504-(4-Phenylbutoxy)styreneAusbeute 62 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 74505Methyltriphenyliphosphonium bromideKatalysatorHCID 8028TetrahydrofuranLösungsmittel2×HCID 8058HexaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of methyltriphenylphosphonium bromide (4.98 g, 13.9 mmol) in anhydrous tetrahydrofuran (130 ml) at 0° C. and under inert atmosphere was added with a 1.6M butyl lithium solution in hexane (8.69 ml) and the mixture was left under stirring at 0° C. for 2 h. After that, a solution of 4-(4-phenylbutoxy)benzaldehyde (2.5 g, 9.84 mmol) in tetrahydrofuran (10 ml) was added and the mixture was left under stirring at room temperature for 36 h, then carefully added with water (20 ml) and extracted with ethyl ether (4×50 ml). The organic extracts were dried and the solvents were evaporated off under reduced pressure. The resulting crude was purified by chromatography through a silica gel column, eluting with petroleum ether:ethyl ether, 95:5, thereby recovering 4.20 g of the title compound (62% yield).

Aufarbeitung

  1. waitthe mixture was left
  2. waitthe mixture was left
  3. stirringunder stirring at room temperature for 36 h
  4. extractionextracted with ethyl ether (4×50 ml)
  5. customThe organic extracts were dried
  6. customthe solvents were evaporated off under reduced pressure
  7. customThe resulting crude was purified by chromatography through a silica gel column
  8. washeluting with petroleum ether

Quellen und Nachweise

ORD-Eintrag
ord-8d51799efc6a428b910662c3291a4696
Quelldatensatz
uspto-grants-1999_11
Patentnummer
US05990142

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