Thionyl Chloride → HCID 54543855, compound
Reaction equation
[C:1]1([C:7]2(CC(O)=O)[O:11][C:10]3[CH:12]=[CH:13][C:14]([Cl:16])=[CH:15][C:9]=3[O:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O=S(Cl)Cl>C1C=CC=CC=1>[CH2:9]([O:8][C:7](=[O:11])[CH2:1][CH2:2][C:7]1([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[O:11][C:10]2[CH:12]=[CH:13][C:14]([Cl:16])=[CH:15][C:9]=2[O:8]1)[CH3:10]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
11.7 g. of (2-phenyl-5-chloro-1,3-benzodioxol-2-yl)-acetic acid mixed with 50 cc. of anhydrous benzene are refluxed with 10 cc. of SOCl2 for 3 hours. The solvent and the excess of SOCl2 are removed under vacuum. The residual oil mixed with 150 cc. of anhydrous ether is added in drops to an ether solution of diazomethane, which is ice cooled to maintain the temperature under 2°-3°C. After 24 h, the ether is removed under vacuum and the residue is mixed with 100 cc. of ethanol. The mixture is heated at 50°C., and 2 g. of Ag2O are added. After 2 hours, the product is treated with animal charcoal, filtered and dried. It is then fractionated and the desired product boils at 200°-207°C./0.4 mm.
Workup
- customThe solvent and the excess of SOCl2 are removed under vacuum
- additionThe residual oil mixed with 150 cc
- additionof anhydrous ether is added in drops to an ether solution of diazomethane, which
- temperaturecooled
- temperatureto maintain the temperature under 2°-3°C
- customthe ether is removed under vacuum
- additionthe residue is mixed with 100 cc
- additionof Ag2O are added
- waitAfter 2 hours
- additionthe product is treated with animal charcoal
- filtrationfiltered
- customdried
Sources & evidence
- ORD record
- ord-d92f4c735836404baf0ea9fa7e23b3ad
- Source dataset
- uspto-grants-1976_07
- Patent number
- US03969368
Reaction notes
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