Thionyl Chloride → 4-Chloro-1-(chloromethyl)-2-methylbenzene
Reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6]O)=[C:4]([CH3:10])[CH:3]=1.S(Cl)([Cl:13])=O>>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][Cl:13])=[C:4]([CH3:10])[CH:3]=1Participants
3
Conditions
- Temperature
- 100 °C
Procedure
Step A A mixture of 4-chloro-2-methylbenzyl alcohol (Aldrich) (5 g, 32 mmol) in thionyl chloride (20 mL) was heated at refluxing (100° C.) for 30 min. The mixture was cooled to room temperature and concentrated. The residue was diluted with ethyl acetate, washed with saturated aqueous NaHCO3 solution, water, brine, dried over MgSO4, and concentrated to give 4-chloro-2-methylbenzyl chloride as a light yellow oil (5.2 g, 93%).
Workup
- temperaturewas heated
- temperatureThe mixture was cooled to room temperature
- concentrationconcentrated
- additionThe residue was diluted with ethyl acetate
- washwashed with saturated aqueous NaHCO3 solution, water, brine
- dry with materialdried over MgSO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-8c4258da90734a7296f2bf2c14e81dc2
- Source dataset
- uspto-grants-2013_01
- Patent number
- US08354444B2
Reaction notes
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