Hydrochloric Acid → 4-(Allyloxy)-4-oxobutanoic acid
Reaction equation
[C:1]1(=[O:7])[O:6][C:4](=[O:5])[CH2:3][CH2:2]1.[CH2:8]([OH:11])[CH:9]=[CH2:10].C(N(CC)C(C)C)(C)C.Cl>ClCCl.CN(C1C=CN=CC=1)C>[C:4]([O:11][CH2:8][CH:9]=[CH2:10])(=[O:5])[CH2:3][CH2:2][C:1]([OH:6])=[O:7]Participants
7
Procedure
To a solution of commercially available succinic anhydride (2.00 g, 20.0 mmol) in dichloromethane (10 ml) were added allyl alcohol (1.75 g, 30.1 mmol), N,N-diisopropylethylamine (3.88 g, 30.1 mmol) and 4-(N,N-dimethylamino)pyridine (10 mg) at room temperature. The mixture was stirred for 1 hour, then 1N hydrochloric acid was added thereto, and the resulting solution was extracted with ethyl acetate. The extract was washed with an aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to afford crude allyl hydrogen succinate.
Workup
- extractionthe resulting solution was extracted with ethyl acetate
- washThe extract was washed with an aqueous solution of sodium chloride
- dry with materialdried over anhydrous magnesium sulfate
- distillationthe solvent was distilled off under reduced pressure
Sources & evidence
- ORD record
- ord-3825b0e78fd6442586d1ada2d78dbda1
- Source dataset
- uspto-grants-2007_06
- Patent number
- US07230023B2
Reaction notes
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