Acetic Acid → 2-[2,3-Dichloro-4-(2-methylenebutyryl)phenoxy]-2-methylpropionic acid
Reaction equation
[Cl:1][C:2]1[C:14]([Cl:15])=[C:13]([C:16](=[O:20])[CH2:17][CH2:18][CH3:19])[CH:12]=[CH:11][C:3]=1[O:4][C:5]([CH3:10])([CH3:9])[C:6]([OH:8])=[O:7].Cl.[CH3:22]NC.C=O.C(O)(=O)C>CN(C)C=O>[Cl:1][C:2]1[C:14]([Cl:15])=[C:13]([C:16](=[O:20])[C:17](=[CH2:22])[CH2:18][CH3:19])[CH:12]=[CH:11][C:3]=1[O:4][C:5]([CH3:10])([CH3:9])[C:6]([OH:8])=[O:7]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of 2-(2,3-dichloro-4-butyrylphenoxy)-2-methylpropionic acid (10 g, 0.031 mole), dimethylamine hydrochloride (15 g, 0.18 mole), paraformaldehyde (3 g, 0.10 equiv.) and acetic acid (0.6 ml) was stirred and heated on a steam bath for two hours. N,N-dimethylformamide (30 ml) was added and stirring and heating was continued for another two hours. The mixture was poured into ice water which was then extracted with ether. The ether extract was washed with water, then brine and finally dried over MgSO4. The ether was evaporated in vacuo and the residue recrystallized from cyclohexane to give 6.3 g 2-[2,3-dichloro-4-(2-methylenebutyryl)phenoxy]-2-methylpropionic acid, m.p. 88°-89° C.
Workup
- temperatureheated on a steam bath for two hours
- stirringstirring
- temperatureheating
- extractionwas then extracted with ether
- extractionThe ether extract
- washwas washed with water
- dry with materialbrine and finally dried over MgSO4
- customThe ether was evaporated in vacuo
- customthe residue recrystallized from cyclohexane
Sources & evidence
- ORD record
- ord-ad810eded95d48d797cdd0796ee7241e
- Source dataset
- uspto-grants-1988_03
- Patent number
- US04731381
Reaction notes
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