4-Hydroxybenzaldehyde → 4-(1-Hexenyl)phenol

HRID 1739483

Reaktionsgleichung

Reaktionsgleichung von HRID 1739483
[Br-].[CH2:2]([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[CH2:3][CH2:4][CH2:5][CH3:6].[Li]N([Si](C)(C)C)[Si](C)(C)C.[OH:36][C:37]1[CH:44]=[CH:43][C:40]([CH:41]=O)=[CH:39][CH:38]=1>C1COCC1>[CH:41]([C:40]1[CH:43]=[CH:44][C:37]([OH:36])=[CH:38][CH:39]=1)=[CH:2][CH2:3][CH2:4][CH2:5][CH3:6]

Komponenten

5

Edukt 3

HCID 1264-HydroxybenzaldehydeHCID 2724565Pentyltriphenylphosphonium bromideHCID 178418261HCID 178418261, Verbindung

Produkt 1

HCID 538311814-(1-Hexenyl)phenolAusbeute 85,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a suspension of pentyl triphenylphosphonium bromide (4.76 g, 11.5 mMol) in freshly distilled THF (40 ml) was added LiN(SiMe3)2 (1N in THF, 23 ml). The red solution was stirred at ambient temperature for 30 minutes then a solution of p-hydroxybenzaldehyde (1.06 g, 10 mMol) in THF (10 ml) added. The reaction was stirred at ambient temperature for 4 days, then partitioned between ethyl ether and dilute aqueous HCl (1N). The combined etherial extracts were washed with brine, dried (MgSO4) and evaporated. The crude oil was purified by chromatography (eluant: ethyl ether/hexane) to give 4-(1-hexenyl)phenol as a pale yellow solid (1.5 g, 85%).

Aufarbeitung

  1. stirringThe reaction was stirred at ambient temperature for 4 days
  2. custompartitioned between ethyl ether and dilute aqueous HCl (1N)
  3. washThe combined etherial extracts were washed with brine
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customThe crude oil was purified by chromatography (eluant: ethyl ether/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-41a8bfd3c65d40f98b729cab42e5078f
Quelldatensatz
uspto-grants-1999_10
Patentnummer
US05965741

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