Ethanol → Ethyl 2-(3,4-dichloroanilino)acetate
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[Cl:13])[NH:5][CH2:6][C:7]([OH:9])=[O:8].[CH2:14](O)[CH3:15].OS(O)(=O)=O>ClC(Cl)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[Cl:13])[NH:5][CH2:6][C:7]([O:9][CH2:14][CH3:15])=[O:8]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 27.5 g (0.125 mol) of 3,4-dichloroanilinoacetic acid, 190 ml of dichloroethane, 15 ml (0.2 mol) of ethanol and 1.5 ml of concentrated H2SO4 is heated for 4 hours under reflux. It is washed with water and with dilute sodium bicarbonate, dried and evaporated to dryness in vacuo. The ester is recrystallised from ethanol and is obtained in a yield of 78%. It melts at 103°-104° C.
Workup
- temperatureunder reflux
- washIt is washed with water and with dilute sodium bicarbonate
- customdried
- customevaporated to dryness in vacuo
- customThe ester is recrystallised from ethanol
- customis obtained in a yield of 78%
Sources & evidence
- ORD record
- ord-aaef4027ebae493392de1591c0e5908f
- Source dataset
- uspto-grants-1980_09
- Patent number
- US04225617
Reaction notes
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