Menthol → Dichloro((1R,2S,5R)-2-isopropyl-5-methylcyclohexyloxy)phosphine

HRID 41825

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

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-418ec2ccf0174a49964151744e04de0f
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08535655B2

Linked notes

Loading…