Water → 6-Benzyloxy-5-tert-butyl-4'-methyl-3-biphenylcarbaldehyde

HRID 2377199Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2377199
[CH2:1]([O:8][C:9]1[C:14]([C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=2)=[CH:13][C:12]([C:22](OC)=[O:23])=[CH:11][C:10]=1[C:26]([CH3:29])([CH3:28])[CH3:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>C(OCC)C.ClCCl.[O-2].[O-2].[Mn+4]>[CH2:1]([O:8][C:9]1[C:14]([C:15]2[CH:16]=[CH:17][C:18]([CH3:21])=[CH:19][CH:20]=2)=[CH:13][C:12]([CH:22]=[O:23])=[CH:11][C:10]=1[C:26]([CH3:29])([CH3:28])[CH3:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

8

Edukt 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 12084817Methyl 6-benzyloxy-5-tert-butyl-4'-methyl-3-biphenylcarboxylateHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 120848186-Benzyloxy-5-tert-butyl-4'-methyl-3-biphenylcarbaldehydeAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418406HCID 178418406, VerbindungKatalysatorHCID 3283Diethyl EtherLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

1 g (2.6 mmol) of methyl 6-benzyloxy-5-tert-butyl-4′-methyl-3-biphenylcarboxylate is dissolved in 40 mL of anhydrous ethyl ether, and the medium is cooled to 0° C. 130 mg (3.3 mmol) of lithium aluminum hydride are added and the reaction medium is stirred for 1 hour. The reaction is hydrolysed by sequential addition of 130 μL of water, 130 μL of 15% sodium hydroxide solution and 400 μL of water. The reaction medium is filtered and the filtrate is concentrated under reduced pressure. The residue obtained is dissolved in 30 mL of dichloromethane, and 2 g (23 mmol) of manganese dioxide are added. The medium is refluxed for 5 hours, and filtered through Celite. A yellow oil is obtained (m=780 mg; yield=85%).

Aufarbeitung

  1. filtrationThe reaction medium is filtered
  2. concentrationthe filtrate is concentrated under reduced pressure
  3. customThe residue obtained
  4. temperatureThe medium is refluxed for 5 hours
  5. filtrationfiltered through Celite
  6. customA yellow oil is obtained (m=780 mg; yield=85%)

Quellen und Nachweise

ORD-Eintrag
ord-ade757147fc0433d88be1d0a13bf61c9
Quelldatensatz
uspto-grants-2008_12
Patentnummer
US07468457B2

Notizen zur Reaktion

Wird geladen…