Toluene → (1S)-4-Methylcyclohex-3-ene-1-carbonyl chloride

HRID 1614923Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1614923
[CH3:1][C:2]1[CH2:7][CH2:6][C@H:5]([C:8]([OH:10])=O)[CH2:4][CH:3]=1.C1(C)C=CC=CC=1.C(Cl)(=O)C([Cl:21])=O>ClCCl.CN(C)C=O>[CH3:1][C:2]1[CH2:7][CH2:6][C@H:5]([C:8]([Cl:21])=[O:10])[CH2:4][CH:3]=1

Komponenten

6

Edukt 3

HCID 1140TolueneHCID 65578Oxalyl chlorideHCID 10877190(1S)-4-methylcyclohex-3-ene-1-carboxylic acid

Produkt 1

HCID 12951476(1S)-4-Methylcyclohex-3-ene-1-carbonyl chloride

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideKatalysatorHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

(1S)-4-Methyl-cyclohex-3-ene-1-carboxylic acid (250 mg, 1.78 mmol), azeotropically dried by evaporation from toluene was dissolved in dichloromethane (4 mL) and treated with dimethylformamide (1 drop). The reaction mixture was cooled to 0° C. and treated dropwise with oxalyl chloride (0.42 mL, 4.5 mmol). The reaction mixture was allowed to warm to ambient temperature while stirring for 4 h. The solution was concentrated, treated with hexanes and concentrated again to afford (1S)-4-methyl-cyclohex-3-ene-1-carboxylic acid chloride as a light yellow oil which was used immediately in the next step.

Aufarbeitung

  1. temperatureto warm to ambient temperature
  2. concentrationThe solution was concentrated
  3. additiontreated with hexanes
  4. concentrationconcentrated again

Quellen und Nachweise

ORD-Eintrag
ord-f1e890d60c44408586cd225a88eb3883
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08765722B2

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