Methanol → HCID 20989487, compound
Reaction equation
[Br:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][CH2:7][C:8]([CH3:14])([CH3:13])[C:9]([O:11]C)=[O:10])=[CH:4][CH:3]=1.[OH-].[Na+].CO>O1CCCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH2:7][C:8]([CH3:13])([CH3:14])[C:9]([OH:11])=[O:10])=[CH:15][CH:16]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
In tetrahydrofuran (40 mL) was dissolved methyl 3-(4-bromophenoxy)-2,2-dimethylpropanoate (3.2 g), 2N aqueous sodium hydroxide solution (10 mL) was added to the solution, and the mixture was stirred at room temperature overnight. After adding methanol (10 mL) to the mixture, the resulting mixture was refluxed for 3 hours. To the residue obtained by concentrating the reaction mixture under reduced pressure were added ethyl acetate and 1N hydrochloric acid, and the liquids were separated. The organic layer was separated, washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain 3-(4-bromophenoxy)-2,2-dimethylpropanoic acid (2.886 g).
Workup
- additionwas added to the solution
- temperaturethe resulting mixture was refluxed for 3 hours
- customTo the residue obtained
- concentrationby concentrating the reaction mixture under reduced pressure
- additionwere added ethyl acetate and 1N hydrochloric acid
- customthe liquids were separated
- customThe organic layer was separated
- washwashed with saturated brine
- dry with materialdried over anhydrous sodium sulfate
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-b7768776d94c4650900f27c58bf0dbb1
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09302996B2
Reaction notes
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