Reaction #1702105

Reaction equation

(1S)-4-Methyl-cyclohex-3-ene-1-carboxylic acid

toluene

oxalyl chloride

→

(1S)-4-methyl-cyclohex-3-ene-1-carboxylic acid chloride

Solvents

dichloromethane

Conditions

Workup

1. 1
   Temperatureto warm to ambient temperature
2. 2
   ConcentrationThe solution was concentrated
3. 3
   workup.ADDITIONtreated with hexanes
4. 4
   Concentrationconcentrated again

Procedure

(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.

Source