Oxalyl chloride → 2-Methylcyclohexanecarbonyl chloride

HRID 2204457Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2204457
[CH3:1][CH:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[C:8]([OH:10])=O.C(Cl)(=O)C([Cl:14])=O>C(Cl)Cl.CN(C=O)C>[CH3:1][CH:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[C:8]([Cl:14])=[O:10]

Komponenten

5

Edukt 2

HCID 65578Oxalyl chlorideHCID 858112-Methylcyclohexanecarboxylic acid

Produkt 1

HCID 27598372-Methylcyclohexanecarbonyl chlorideAusbeute 102,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 2-methylcyclohexanecarboxylic acid (6.00 mL, 42.6 mmol, mixture of cis and trans) in DCM (60 mL) was added oxalyl chloride (4.80 mL, 55.3 mmol) followed by DMF (0.03 mL, 0.4 mmol). The reaction mixture was stirred at ambient temperature for about 4 h before it was concentrated under reduced pressure to constant weight to afford 2-methylcyclohexanecarbonyl chloride (mixture of diastereomers) as a yellow oil (7.0 g, 97%): 1H NMR (400 MHz, CDCl3) δ 2.98-2.94 (m, 1H), 2.39-2.35 (m, 1H), 1.91-1.82 (m, 1H), 1.79-1.72 (m, 1H), 1.69-1.60 (m, 2H), 1.57-1.47 (m, 2H), 1.42-1.36 (m, 1H), 1.34-1.26 (m, 1H), 1.04-0.96 (m, 3H).

Aufarbeitung

  1. concentrationwas concentrated under reduced pressure to constant weight

Quellen und Nachweise

ORD-Eintrag
ord-53637888526143f384cf31a59bb0de1c
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09365579B2

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