Sulfuric Acid → 2-(2-Chlorobenzylideneaminooxymethyl)-2-methylpropanoic acid
Reaction equation
S(=O)(=O)(O)O.[Cl:6][C:7]1[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=1[CH:9]=O.[CH3:15][C:16]1([CH3:22])[CH2:20][O:19][NH:18][C:17]1=[O:21].C(=O)(O)[O-:24].[Na+]>C1(C)C=CC=CC=1>[Cl:6][C:7]1[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=1[CH:9]=[N:18][O:19][CH2:20][C:16]([CH3:22])([CH3:15])[C:17]([OH:24])=[O:21]Participants
Procedure
Concentrated sulfuric acid (4 mL) was added to a stirred mixture of 2-chlorobenzaldehyde (24.5 grams; 0.174 mole) and 4,4-dimethyl-3-isoxazolidinone (20.1 grams; 0.174 mole) in toluene (150 mL) cooled in an ice bath and under a nitrogen atmosphere. Upon completion of addition, the reaction mixture was stirred at ambient temperature overnight under a nitrogen atmosphere. The reaction mixture was then neutralized by the careful addition of solid sodium bicarbonate and then extracted with aqueous sodium bicarbonate (3×500 mL). The combined aqueous extracts were acidified to pH 3 with concentrated hydrochloric acid and then extracted with methylene chloride (3×150 mL). The dried (sodium sulfate) organic layer was concentrated under reduced pressure to afford 16 grams of 2-(2-chlorobenzylideneaminooxymethyl)-2-methylpropanoic acid as a solid, m.p. 78°-80° C.
Workup
- temperaturecooled in an ice bath and under a nitrogen atmosphere
- additionUpon completion of addition
- extractionextracted with aqueous sodium bicarbonate (3×500 mL)
- extractionextracted with methylene chloride (3×150 mL)
- dry with materialThe dried (sodium sulfate) organic layer
- concentrationwas concentrated under reduced pressure
Sources & evidence
- ORD record
- ord-bbc644e2f73b4e5fa45f597650aa8799
- Source dataset
- uspto-grants-1989_08
- Patent number
- US04855480
Reaction notes
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