Phosphoric Acid → Ethyl 6-(acetyloxy)hexanoate
Reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8].[C:12](OC(=O)C)(=[O:14])[CH3:13].P(=O)(O)(O)O>CCCCCC>[C:12]([O:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])(=[O:14])[CH3:13]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
240 g of ethyl 6-hydroxy-hexanoate are placed in a round flask which is provided with a dropping funnel, a thermometer and a stirrer. A mixture of 180 g of acetic anhydride and 3 g of 85% phosphoric acid is added dropwise thereto within a half hour while stirring. During the addition the temperature is held at 25° C. by cooling. Thereafter, the reaction mixture is heated slowly to 50° C. and held at this temperature for 3 hours. After cooling the mixture is treated with ice-water and taken up in 500 ml of hexane. The hexane solution is washed with water, with 100 ml of a 10% sodium carbonate solution and thereupon neutral with water. After drying over sodium sulphate the solvent is distilled off. 282 g of crude product are obtained. Fractional distillation gives 223 g (yield 73.7% of theory) of chemically pure ethyl 6-acetoxy-hexanoate; 190 g thereof can be used as an olfactorily pure product without further treatment.
Workup
- customwhich is provided with a dropping funnel
- additionis added dropwise
- additionDuring the addition the temperature
- customis held at 25° C.
- temperatureby cooling
- temperatureAfter cooling the mixture
- washThe hexane solution is washed with water, with 100 ml of a 10% sodium carbonate solution
- dry with materialAfter drying over sodium sulphate the solvent
- distillationis distilled off
- custom282 g of crude product are obtained
- distillationFractional distillation
Sources & evidence
- ORD record
- ord-c4b32cfa65db4299ac613de58d531eba
- Source dataset
- uspto-grants-1987_05
- Patent number
- US04668433
Reaction notes
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