Thionyl Chloride → 2-(3,4,5-trimethoxyphenyl)acetyl Chloride
Reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:13][C:14]([OH:16])=O)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].S(Cl)([Cl:19])=O>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:13][C:14]([Cl:19])=[O:16])[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10]Participants
Conditions
- Temperature
- 0 °C
Procedure
3,4,5-trimethoxy phenyl acetic acid (9.5 g, 0.042 mol) was added slowly to the thionyl chloride (15 g, 0.126 mol) cooled to 0° C., and warmed to room temperature, then stirred for 3 hours. Residual thionyl chloride was distilled out to obtain 3,4,5-trimethoxy phenyl acetic acid chloride (10.3 g, 0.042 mol). Thymol (6.3 g, 0.042 mol) and triethylamine (6.4 g, 0.063 mol) were dissolved in 200 ml of dichloromethane and stirred, and then the above 3,4,5-trimethoxy phenyl acetic acid chloride (10.3 g) dissolved in 50 ml of dichloromethane was added thereto drop by drop. After the reaction was completed, reaction solution was condensed, and 500 ml of ethyl acetate was added to dissolve the reaction mixture. The resultant was washed with distilled water twice, dried with anhydrous sodium sulfate, then filtered and condensed, and finally proceeded to column chromatography to obtain 9.0 g (Yield=60%) of white solid state of the object product.
Workup
- temperaturewarmed to room temperature
- distillationResidual thionyl chloride was distilled out
Sources & evidence
- ORD record
- ord-8b27ac2f69dd48589e4a1ca039702e2b
- Source dataset
- uspto-grants-2009_04
- Patent number
- US07517911B2
Reaction notes
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