Toluene → (1S)-4-Methylcyclohex-3-ene-1-carbonyl chloride
Reaction equation
[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]=1Participants
6
Conditions
- Temperature
- 0 °C
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.
Workup
- temperatureto warm to ambient temperature
- concentrationThe solution was concentrated
- additiontreated with hexanes
- concentrationconcentrated again
Sources & evidence
- ORD record
- ord-9e84cdbf6a9b4fec9af22add883276ed
- Source dataset
- uspto-grants-2013_08
- Patent number
- US08501714B2
Reaction notes
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