Menthol → Dichloro((1R,2S,5R)-2-isopropyl-5-methylcyclohexyloxy)phosphine
Reaction equation
[P:1]([Cl:4])(Cl)[Cl:2].[CH:5]1([CH3:15])[CH2:10][CH2:9][CH:8]([CH:11]([CH3:13])[CH3:12])[CH:7]([OH:14])[CH2:6]1>ClCCl>[Cl:2][P:1]([Cl:4])[O:14][C@@H:7]1[CH2:6][C@H:5]([CH3:15])[CH2:10][CH2:9][C@H:8]1[CH:11]([CH3:13])[CH3:12]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -30 °C
Procedure
The phosphorus trichloride (56.0 ml, 87.89 g, 0.640 mol) was added to dichloromethane (anhydrous) under argon gas to obtain a solution. The solution was cooled to −30° C. and (−)-menthol (1R,2S,5R) (10.00 g, 0.0640 mol) was added portion wise over 10 mins. The solution was allowed to warm to ambient temperature and was allowed to stir at ambient temperature for 16 hours. The solvent was removed in vacuo to obtain a colourless oil (16.46 g). The crude product was used directly in the subsequent step.
Workup
- customto obtain a solution
- temperatureto warm to ambient temperature
- customThe solvent was removed in vacuo
Sources & evidence
- ORD record
- ord-dcbbc9df85044f0780fd04a05ab58c03
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09408919B2
Reaction notes
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