Aspirin → HCID 15341562, compound
Reaction equation
[C:1]([O:4][C:5]1[CH:13]=[CH:12][CH:11]=[CH:10][C:6]=1[C:7]([OH:9])=[O:8])(=[O:3])[CH3:2].C(N(CC)CC)C.ClC(OCC)=O.[CH3:27][C:28]1([CH3:35])[O:32][CH:31]([CH2:33]O)[CH2:30][O:29]1>ClCCl.O>[C:1]([O:4][C:5]1[CH:13]=[CH:12][CH:11]=[CH:10][C:6]=1[C:7]([O:9][CH2:33][CH:31]1[CH2:30][O:29][C:28]([CH3:35])([CH3:27])[O:32]1)=[O:8])(=[O:3])[CH3:2]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
The solution from 2-acetoxybenzoic acid (10.0 g, 55.5 mmol) in dichloromethane (200 ml) is treated with triethylamine (7.7 ml, 55.5 mmol), cooled to 0° C., treated dropwise with ethyl chloroformate (5.3 ml, 55.5 mmol), stirred at 0° C. for 1 h and filtered. The filtrate is added at room temperature to a solution of (±)-2,2-dimethyl-4-hydroxymethyl-1,3-dioxolane (7.33 g, 55.5 mmol) and triethylamine (50 ml) in dichloromethane (100 ml). After 4 h, water (50 ml) is added and the mixture is stirred. The organic phase is washed with dilute hydrochloric acid, saturated aqueous sodium hydrogencarbonate solution and water, dried over magnesium sulphate and concentrated. The residue is purified by column chromatography on silica gel 60 (hexane/ethyl acetate =15/1). Yield: 8.4 g.
Workup
- filtrationfiltered
- waitAfter 4 h
- stirringthe mixture is stirred
- washThe organic phase is washed with dilute hydrochloric acid, saturated aqueous sodium hydrogencarbonate solution and water
- dry with materialdried over magnesium sulphate
- concentrationconcentrated
- customThe residue is purified by column chromatography on silica gel 60 (hexane/ethyl acetate =15/1)
Sources & evidence
- ORD record
- ord-8457430ff45f4028b760b543f0a4ee8a
- Source dataset
- uspto-grants-1999_01
- Patent number
- US05859053
Reaction notes
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