Cyclohexanecarboxaldehyde, 4-(1,1-dimethylethyl)- → HCID 178445649, Verbindung

HRID 653971

Reaktionsgleichung

Reaktionsgleichung von HRID 653971
[CH3:1][C:2]([CH:5]1[CH2:10][CH2:9][CH:8]([CH:11]=[O:12])[CH2:7][CH2:6]1)([CH3:4])[CH3:3].C[O-].[Na+]>CO>[CH3:4][C:2]([C@H:5]1[CH2:6][CH2:7][C@H:8]([CH:11]=[O:12])[CH2:9][CH2:10]1)([CH3:1])[CH3:3]

Komponenten

4

Edukt 2

HCID 88655Cyclohexanecarboxaldehyde, 4-(1,1-dimethylethyl)-HCID 10942334Sodium Methoxide

Produkt 1

HCID 178445649HCID 178445649, VerbindungAusbeute 80,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of the 4-(1,1-dimethylethyl)cyclohexanecarboxaldehyde (862 mg, 5.12 mmol) as obtained above in CH3OH (44 mL) at room temperature was added dropwise sodium methoxide (1.44 mL of 25% by weight, ~4.73M, 6.29 mmol). After stirring for 3 hrs at room temperature, the reaction was quenched by addition of glacial HOAc-ether (1:3) dropwise until the pH was 6-7 followed by addition of a few drops of sat. NaHCO3. The CH3OH was removed under reduced pressure and the residue was partitioned between EtOAc (200 mL deoxygenated by passage of argon) and brine (40 mL). The aqueous layer was extracted with EtOAc (50 mL) and the combined organic extracts were dried (Na2SO4) and concentrated to give crude product (1.6 g). Purification by flash chromatography, eluting with 25% EtOAc/hexane gave trans-4-(1,1-dimethylethyl)cyclohexanecarboxaldehyde (690 mg, 4.1 mmol) in 80% yield.

Aufarbeitung

  1. customthe reaction was quenched by addition of glacial HOAc-ether (1:3) dropwise until the pH was 6-7
  2. additionfollowed by addition of a few drops of sat. NaHCO3
  3. customThe CH3OH was removed under reduced pressure
  4. customthe residue was partitioned between EtOAc (200 mL deoxygenated by passage of argon) and brine (40 mL)
  5. extractionThe aqueous layer was extracted with EtOAc (50 mL)
  6. dry with materialthe combined organic extracts were dried (Na2SO4)
  7. concentrationconcentrated
  8. customto give crude product (1.6 g)
  9. customPurification by flash chromatography
  10. washeluting with 25% EtOAc/hexane

Quellen und Nachweise

ORD-Eintrag
ord-aef30e7a1a1d46cc8e4077b4350ba8d3
Quelldatensatz
uspto-grants-1992_07
Patentnummer
US05128448

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