Reaction equation
[OH-].[Na+].[Cl:3][C:4]1[C:9]([Cl:10])=[CH:8][C:7]([Cl:11])=[CH:6][C:5]=1[OH:12].Br[CH:14]([CH2:18][CH3:19])[C:15]([OH:17])=[O:16]>>[Cl:3][C:4]1[C:9]([Cl:10])=[CH:8][C:7]([Cl:11])=[CH:6][C:5]=1[O:12][CH:14]([CH2:18][CH3:19])[C:15]([OH:17])=[O:16]Participants
Conditions
- Temperature
- 15 °C
Procedure
44.0 g (0.55 mole) of 50% aqueous sodium hydroxide was added to a mixture of 42.5 g (0.22 mole) of 2,3,5-trichlorophenol and 43.4 g (0.26 mole) of 2-bromobutyric acid, with rapid stirring at an initial temperature of 15° C. The temperature rose to 45° C over the course of the addition during which time a cold water bath was applied. At the completion of the sodium hydroxide addition, the cold bath was removed and the mixture was heated to 110° C for a 15-minute period. Then 50 ml of water, 53 ml of perchloroethylene, and 42 ml of concentrated hydrochloric acid were added and the mixture was heated to 85° C, then phase-separated. The organic layer was cooled and the product, α-(2,3,5-trichlorophenoxy)butyric acid, crystallized. The acid was isolated by filtration to give 43.1 g (69.1% yield) of α-(2,3,5-trichlorophenoxy)butyric acid, m.p. 106°-114° C.
Workup
- additionThe temperature rose to 45° C over the course of the addition during which time a cold water bath
- customthe cold bath was removed
- temperaturethe mixture was heated to 110° C for a 15-minute period
- additionThen 50 ml of water, 53 ml of perchloroethylene, and 42 ml of concentrated hydrochloric acid were added
- temperaturethe mixture was heated to 85° C
- customphase-separated
- temperatureThe organic layer was cooled
- customthe product, α-(2,3,5-trichlorophenoxy)butyric acid, crystallized
- customThe acid was isolated by filtration
Sources & evidence
- ORD record
- ord-eb07ab66c338484ab77495dd29710c46
- Source dataset
- uspto-grants-1977_01
- Patent number
- US04001427
Linked notes
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