Hydrochloric Acid → (3-(Chlorocarbonyl)-2-methylphenyl)acetate
Reaction equation
[C:1]([O:4][C:5]1[C:6]([CH3:14])=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8](O)=[O:9])(=[O:3])[CH3:2].S(Cl)([Cl:17])=O.Cl>C1(C)C(C)=CC=CC=1>[C:1]([O:4][C:5]1[C:6]([CH3:14])=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8]([Cl:17])=[O:9])(=[O:3])[CH3:2]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
In a flask, 60.0 g of 3-acetoxy-2-methylbenzoic acid are suspended under nitrogen in 140.0 g of xylene. The suspension is heated to 70° C. and 42.9 g of thionyl chloride are added dropwise. The mixture is heated further. At approx. 75° C., vigorous gas evolution (SO2, HCl) commences. The liquid phase temperature rises continuously and reaches 108° C. after approx. 4 h. The solution is cooled to approx. 50° C. under nitrogen and the reflux condenser is replaced by Vigreux column. At atmospheric pressure and later under reduced pressure, first xylene and thionyl chloride residues and then the product are distilled over. The product distills over at 15 mbar and 147.0-148.0° C. 59.6 g of 3-acetoxy-2-methylbenzoyl chloride (97.3%) are obtained. This corresponds to 91.0% of theory.
Workup
- temperatureThe mixture is heated further
- customAt approx. 75° C.
- temperatureThe solution is cooled to approx. 50° C. under nitrogen
- distillationAt atmospheric pressure and later under reduced pressure, first xylene and thionyl chloride residues and then the product are distilled over
- distillationThe product distills over at 15 mbar and 147.0-148.0° C
Sources & evidence
- ORD record
- ord-d67a096240fb4e09b213bad8477b1b83
- Source dataset
- uspto-grants-2005_05
- Patent number
- US06891060B2
Reaction notes
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