Glutaric anhydride → 5-(Tert-butoxy)-5-oxopentanoic acid
Reaction equation
[C:1]1(=[O:8])[O:7][C:5](=[O:6])[CH2:4][CH2:3][CH2:2]1.[CH3:9][C:10]([CH3:13])([O-:12])[CH3:11].[K+]>O1CCCC1>[C:10]([O:12][C:5](=[O:6])[CH2:4][CH2:3][CH2:2][C:1]([OH:7])=[O:8])([CH3:13])([CH3:11])[CH3:9]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 40 °C
Procedure
Glutaric anhydride (11.41 g.) was added portion-wise to a solution of potassium tert-butoxide (14.02 g.) in tetrahydrofuran (100 ml.) at ambient temperature. After the exothermic reaction was ceased, the reaction mixture was stirred at 40° C. for 15 minutes. Tetrahydrofuran was distilled off under reduced pressure. The residue was dissolved in water. After ethyl acetate was added, the solution was adjusted to pH 9 with aqueous potassium carbonate solution under ice-cooling. The separated water layer was washed with ethyl acetate, treated with activated charcoal, overlapped with ethyl acetate, and then adjusted to pH 4.0 with 10% hydrochloric acid under ice-cooling. The ethyl acetate layer was dried over magnesium sulfate, treated with activated charcoal, filtered and concentrated under reduced pressure to give glutaric acid mono-tert-butyl ester (10 g.).
Workup
- customAfter the exothermic reaction
- distillationTetrahydrofuran was distilled off under reduced pressure
- dissolutionThe residue was dissolved in water
- additionAfter ethyl acetate was added
- temperaturecooling
- washThe separated water layer was washed with ethyl acetate
- additiontreated with activated charcoal
- temperaturecooling
- dry with materialThe ethyl acetate layer was dried over magnesium sulfate
- additiontreated with activated charcoal
- filtrationfiltered
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-30d13773bc354896ab81d0f825a8eff8
- Source dataset
- uspto-grants-1982_09
- Patent number
- US04349552
Reaction notes
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