Hydrochloric Acid → Succinic mono-(2-{2-[2-(2-allyloxy-ethoxy)-ethoxy]-ethoxy}-ethyl)ester
Reaction equation
[CH2:1]([O:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][O:10][CH2:11][CH2:12][O:13][CH2:14][CH2:15][OH:16])[CH:2]=[CH2:3].[C:17]1(=[O:23])[O:22][C:20](=[O:21])[CH2:19][CH2:18]1.N1C=CC=CC=1.Cl>CN(C1C=CC=CN=1)C.C1(C)C=CC=CC=1>[CH2:1]([O:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][O:10][CH2:11][CH2:12][O:13][CH2:14][CH2:15][O:16][C:17](=[O:23])[CH2:18][CH2:19][C:20]([OH:22])=[O:21])[CH:2]=[CH2:3]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 80 °C
Procedure
2-{2-[2-(2-allyloxy-ethoxy)-ethoxy]-ethoxy}-ethanol (9) (3.6 g, 15 mmol), succinic anhydride (1.8 g, 18 mmol), pyridine (1.22 mL, 15 mmol), dimethylaminopyridine (183 mg, 10 mol %), and dry toluene (5 mL) were charged into a screw cap culture tube. The mixture was stirred at 80° C. for 10 hours. Next, the reaction was stopped by adding 10% HCl (6 mL) and the reaction mixture was extracted with CH2Cl2 (3×10 mL). An organic layer was collected and dried on MgSO4. AMBERLITE™ resin IR-120 (+) (2 g) was added and stirred to perform ion exchange. The resin was filtered off and the filtrate was concentrated to obtain yellow oil (5.2 g, 92%). The compound was used without further purification. The NMR analysis result of the compound is as follows.
Workup
- customcap culture tube
- extractionthe reaction mixture was extracted with CH2Cl2 (3×10 mL)
- customAn organic layer was collected
- customdried on MgSO4
- additionwas added
- stirringstirred
- filtrationThe resin was filtered off
- concentrationthe filtrate was concentrated
Sources & evidence
- ORD record
- ord-dad9215693bb4484abeb348fbc47530a
- Source dataset
- uspto-grants-2010_05
- Patent number
- US07718577B2
Reaction notes
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