1-Methyl-2-(1-methylethenyl)cyclobutaneethanol → HCID 15225559, Verbindung

HRID 861205Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 861205
[CH3:1][C:2]1([CH2:9][CH2:10][OH:11])[CH2:5][CH2:4][CH:3]1[C:6]([CH3:8])=[CH2:7].CC1(CC=[O:22])CCC1C(C)=C.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>>[CH3:1][C:2]1([CH2:9][C:10]([OH:22])=[O:11])[CH2:5][CH2:4][CH:3]1[C:6]([CH3:8])=[CH2:7]

Komponenten

4

Edukt 3

HCID 1173141-Methyl-2-(1-methylethenyl)cyclobutaneethanolHCID 15225560HCID 15225560, VerbindungHCID 178418287HCID 178418287, Verbindung

Produkt 1

HCID 15225559HCID 15225559, Verbindung

Versuchsvorschrift

A four gram sample of racemic 1-methyl-2-(1-methylethenyl)-cyclobutaneethanol (grandisol I) [2] (Bedoukian, Inc.) was oxidized to the corresponding racemic aldehyde, 1-methyl-2-(1-methylethenyl)-cyclobutaneacetaldehyde (grandisal) using pyridinium chlorochromate (Webster) (3.4 g, % yield 86.1). The racemic aldehyde was distilled under vacuum and a 3 gram sample was subsequently oxidized to racemic 1 using AgNO3 and NaOH (Pickett): nearly colorless oil (1.23 g, % yield 32.2); eims m/z (rel. int. %) 168 (1), 125 (12), 109 (14), 108 (35), 93 (9), 91 (3), 81 (6), 79 (11), 77 (10), 69 (11), 68 (100), 67 (86), 55 (11), 53 (30), 43 (35), 41 (41); H NMR (CDCl3) δ 2.61 (1H, m, H-2), 1.83 (1H, m, H-3a), 1.95 (1H, m, H-3b), 1.71 (1H, m, H-4a), 1.95 (1H, m, H-4b), 1.31 (3H, s, Me-5), 2.03 (1H, dd, J=14.6,H-6a), 2.54 (1H, d, J=14.6, H-6b), 4.85 (1H, m, H-9a), 4.65 (1H, m, H-9b), 1.64 (3H, s, Me-10); 13C NMR (CDCl3) δ 41.1 (C-1), 51.9 (C-2), 18.7 (C-3), 29.0 (C-4), 27.9 (C-5), 38.5 (C-6), 179.7 (C-7), 144.1 (C-8), 110.3 (C-9), 22.8 (C-10).

Aufarbeitung

  1. distillationThe racemic aldehyde was distilled under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-b31c2d235bb74fa4bbf6c7138e3a8877
Quelldatensatz
uspto-grants-1998_02
Patentnummer
US05714139

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