Thionyl Chloride → Acetyl chloride, (benzoyloxy)-
Reaction equation
[C:1]([O:9][CH2:10][C:11]([OH:13])=O)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)([Cl:16])=O>>[C:1]([O:9][CH2:10][C:11]([Cl:16])=[O:13])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
3
Procedure
A mixture of benzoyloxyacetic acid (5.4 g.) and thionyl chloride (50 ml.) was stirred at 70°-80° C. for an hour and then excess thionyl chloride was distilled off under reduced pressure to give benzoyloxyacetyl chloride. A solution of benzoyloxyacetylchloride obtained above in acetone (10 ml.) was added dropwise to a solution of 3-(N-hydroxyamino)propylphosphonic acid (1.64 g.) in a mixture of water (16 ml.) and acetone (20 ml.) over 30 minutes interval with stirring under ice-cooling and maintaining carefully the pH at around 7-8, together with by adding dropwise a 5% aqueous sodium bicarbonate solution and stirring was continued for additional 30 minutes.
Workup
- distillationexcess thionyl chloride was distilled off under reduced pressure
Sources & evidence
- ORD record
- ord-06af5b4d9cc54b2cb377f17a98969351
- Source dataset
- uspto-grants-1980_01
- Patent number
- US04182758
Reaction notes
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