N,N-Dimethylaniline → HCID 20200020, compound
Reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8].CN(C)C1C=CC=CC=1.Cl[C:22]([O:24][CH2:25][CH3:26])=[O:23]>C1(C)C=CC=CC=1>[CH2:25]([O:24][C:22]([O:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:23])[CH3:26]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
160 g of ethyl 6-hydroxy-hexanoate, 145.4 g of N,N-dimethylaniline and 200 ml of anhydrous toluene are placed in a round flask which is provided with a dropping funnel, a thermometer and a stirrer. 119.4 g of ethyl chloroformate are added dropwise at 25° C. within a half hour while stirring. The reaction mixture is held under reflux for 3 hours. After cooling the reaction mixture is poured on to ice-water, the organic phase is washed twice with water, with 100 ml of a 5% hydrochloric acid solution and then neutral with water. After drying over sodium sulphate the solvent is distilled off. 173 g of crude product are obtained. Fractional distillation gives 112 g (yield 48.3% of theory) of chemically pure ethyl 6-ethoxycarbonyloxy-hexanoate; 75 g thereof can be used as an olfactorily pure product without further treatment.
Workup
- customwhich is provided with a dropping funnel
- temperatureunder reflux for 3 hours
- temperatureAfter cooling the reaction mixture
- washthe organic phase is washed twice with water, with 100 ml of a 5% hydrochloric acid solution
- dry with materialAfter drying over sodium sulphate the solvent
- distillationis distilled off
- custom173 g of crude product are obtained
- distillationFractional distillation
Sources & evidence
- ORD record
- ord-81cf8ea596da49babe5b8a2cc6bdcf8a
- Source dataset
- uspto-grants-1987_05
- Patent number
- US04668433
Reaction notes
Loading…