Acetic acid--water (1/1) → Citronellal

Temperature

0 °C

Precursor complex: [Rh(COD)2 ]+X- (X=anion as defined above) In a glove box, a solution of 0.025 mmole of the respective precursor complex (for example [Rh(COD)2 ]+SO3CF3-) in 2.5 ml of THF (0.01 M) was added to 0.025 mmole of the respective ligand in a one-necked flask equipped with a stopcock. The solution was stirred for 1 h, then a solution of 10 mmole of diethylgeranylamine or diethylnerylamine in 10 ml of the respective solvent was added. The flask was then equipped with a reflux condenser connected to a Schlenk line, the apparatus was purged with argon and the solution brought to reflux. Reaction temperature was held constant during the reaction time indicated in the table. The mixture was then cooled to 0° C. before adding 5 ml of a 1:4 of acetic acid/water. The reaction mixture was raised to room temperature and the solution extracted with diethyl ether. The extract was washed with water (10 ml), 15% NaOH solution (2×10 ml), then neutralized with water and thereafter dried over MgSO4. After concentration of the resulting solution, the residue was distilled in a bulb-to-bulb apparatus to give optically active citronellal and with the conversions and ee's as indicated in the tables below.

1. customequipped with a stopcock
2. customThe flask was then equipped with a reflux condenser
3. customconnected to a Schlenk
4. customline, the apparatus was purged with argon
5. temperatureto reflux
6. customReaction temperature
7. temperatureThe reaction mixture was raised to room temperature
8. extractionthe solution extracted with diethyl ether
9. washThe extract was washed with water (10 ml), 15% NaOH solution (2×10 ml)
10. dry with materialdried over MgSO4
11. distillationAfter concentration of the resulting solution, the residue was distilled in a bulb-to-bulb apparatus

ORD record

ord-02343fa1551d49ba8e25ec24eddb215e

Source dataset

uspto-grants-2000_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06020527