Ethanol → 5-(2,2,3-Trimethylcyclopent-3-en-1-yl)-pentan-2-ol

HRID 972173Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 972173
[CH3:1][CH:2]([OH:6])[CH:3]=[CH:4][CH3:5].[CH:7](O)=[CH:8][CH2:9][CH2:10][CH3:11].[CH2:13](O)[CH2:14]CCC.[H][H].[CH2:21](O)C>[Pd]>[CH3:11][C:10]1([CH3:21])[C:13]([CH3:14])=[CH:7][CH2:8][CH:9]1[CH2:5][CH2:4][CH2:3][CH:2]([OH:6])[CH3:1]

Komponenten

6

Edukt 4

HCID 702EthanolHCID 15289(+-)-3-Penten-2-olHCID 86735115Pentenol pentanolHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 212172375-(2,2,3-Trimethylcyclopent-3-en-1-yl)-pentan-2-olAusbeute 77,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 23938PalladiumKatalysator

Versuchsvorschrift

A mixture of 0.6 g of 5% palladium on carbon, 44.1 g (0.15 moles of the pent-3-en-2-ol) of the above pentenol/pentanol mixture and 50 ml of ethanol was hydrogenated at 25°-45° C and 35-52 psi until hydrogen uptake ceased. The mixture was filtered to remove the catalyst and the solvent was removed from the filtrate by distillation. The residual oil was fractionally distilled to yield 5-(2,2,3-trimethylcyclopent-3-en-1-yl)-pentan-2-ol 30.1 g (77.7% yield); bp 105-108° C (1.5 mm); mol wt. 196 (ms); ir, 3350 (s, broad), 3040 and 797 cm-1 ; nmr, 0.5δ, 0.8, 0.9 and 1.0 (6H, 4s, geminal dimethyl groups of various diastereomers in the mixture), 1.2 (3H, d, J~6 Hz, carbinol methyl), 1.3-1.5 (7H, broad complex), 1.6 (3H, broad s, olefinic methyl), 1.7-2.4 (3H, broad complex containing 1H exchangeable with D2O), 3.8 (1H, broad multiplet, carbinyl H), 5.2 (1H, broad multiplet, olefinic H).

Aufarbeitung

  1. customwas hydrogenated at 25°-45° C
  2. filtrationThe mixture was filtered
  3. customto remove the catalyst
  4. customthe solvent was removed from the filtrate by distillation
  5. distillationThe residual oil was fractionally distilled

Quellen und Nachweise

ORD-Eintrag
ord-1729ba4644a74729bfb68a7289f9da8b
Quelldatensatz
uspto-grants-1977_10
Patentnummer
US04052341

Notizen zur Reaktion

Wird geladen…