Acetic Anhydride → HCID 21832202, compound
Reaction equation
[C:1]([O:4][C:5](=[O:7])[CH3:6])(=O)[CH3:2].[O:8]=[C:9]([CH3:21])[CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15](CCO)=[CH:14][CH:13]=1.O1CCCC1>N1C=CC=CC=1>[C:5]([O:4][CH2:1][CH2:2][C:15]1[CH:16]=[CH:17][C:12]([O:11][CH2:10][C:9](=[O:8])[CH3:21])=[CH:13][CH:14]=1)(=[O:7])[CH3:6]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
1.96 g of acetic anhydride were added, whilst ice-cooling, to a mixture of 3.1 g of 2-[4-(2-oxopropoxy)phenyl]ethanol (prepared as described in Preparation 7), 50 ml of anhydrous tetrahydrofuran and 2.53 g of pyridine, and the resulting mixture was stirred at room temperature for 3.5 hours. At the end of this time, 12.5 g of pyridine and 9.8 g of acetic anhydride were added, whilst ice-cooling, and the mixture was allowed to stand at room temperature for 1 day, after which the solvent was removed by distillation under reduced pressure, and the residue was mixed with water and then extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate, and the solvent was removed by distillation under reduced pressure, to give the title compound having an Rf=0.71 (thin layer chromatography over silica gel, using a 1:1 by volume mixture of ethyl acetate and hexane as the developing solvent).
Workup
- temperaturecooling
- waitto stand at room temperature for 1 day
- customafter which the solvent was removed by distillation under reduced pressure
- additionthe residue was mixed with water
- extractionextracted with ethyl acetate
- dry with materialThe extract was dried over anhydrous sodium sulfate
- customthe solvent was removed by distillation under reduced pressure
Sources & evidence
- ORD record
- ord-ee57079383a24d4a91179cb66056a734
- Source dataset
- uspto-grants-1996_11
- Patent number
- US05576340
Reaction notes
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