Hydrochloric Acid → 3-(3,4-dichlorophenyl)-2-oxopropanoic acid
Reaction equation
Cl.C(N[C:6](=[CH:10][C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([Cl:18])[CH:12]=1)[C:7]([OH:9])=[O:8])(=O)C.[OH2:19].C1(C)C=CC=CC=1>CN1CCCC1=O>[Cl:18][C:13]1[CH:12]=[C:11]([CH2:10][C:6](=[O:19])[C:7]([OH:9])=[O:8])[CH:16]=[CH:15][C:14]=1[Cl:17]Participants
Conditions
- Temperature
- 125 °C
Procedure
140 mL 4 M HCl were added to a suspension of 21.0 g (76.6 mmol) 2-acetylamino-3-(3,4-dichloro-phenyl)-acrylic acid in 100 mL N-methyl-2-pyrrolidinone and the reaction mixture was then heated for 4 h at an oil bath temperature of 125° C. The cooled reaction solution was poured onto a cooled mixture of 350 mL water and 120 mL toluene. The phases were separated, the aqueous phase was again extracted with toluene, the combined organic phases were extracted with water, filtered through Na2SO4 and evaporated down i. vac. The residue was taken up in 1 M NaOH and washed twice with diethyl ether. The aqueous phase was acidified with 2 M HCl and extracted three times with EtOAc. The combined organic phases were filtered through Na2SO4 and evaporated down i. vac. The residue was combined with diethyl ether, suction filtered and dried in the vacuum drying cupboard.
Workup
- customThe cooled reaction solution
- customThe phases were separated
- extractionthe aqueous phase was again extracted with toluene
- extractionthe combined organic phases were extracted with water
- filtrationfiltered through Na2SO4
- customevaporated down i
- washwashed twice with diethyl ether
- extractionextracted three times with EtOAc
- filtrationThe combined organic phases were filtered through Na2SO4
- customevaporated down i
- filtrationfiltered
- customdried in the vacuum
- customdrying cupboard
Sources & evidence
- ORD record
- ord-42cf452218e943dbab968ef9fcf8e669
- Source dataset
- uspto-grants-2010_04
- Patent number
- US07700598B2
Reaction notes
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