Chemical Properties
white to off-white crystals
Uses
(1
S,2
S)-trans-1,2-Cyclohexanediol may be used in the preparation of (1
S,2
S)-1,2-cyclohexanediyl bis(4-vinylbenzoate) by reacting with 4-vinylbenzoyl chloride. It may also be used as a chiral ligand for the preparation of non-racemic hydroxy phosphonates via titanium alkoxide-catalyzed addition of dimethyl phosphite to the corresponding aldehydes.
Purification Methods
The enantiomers have been recrystallised from *C6H6 or EtOAc. The (±) diol has been resolved via the distrychnine salt of the hemisulfate [Hayward et al. J Chem Soc Perkin Trans 1 2413 1976], or the 1-menthoxy acetates. {l-trans-diastereoisomer has m 64o, []D -91.7o (c 1.4 EtOH) from pet ether or aqueous EtOH and yields the (-)-trans-diol } and {d-trans-diastereoisomer has m 126-127o, []D -32.7o (c 0.8 EtOH) from pet ether or aqueous EtOH and yields the (+)-trans diol}. The bis-4-nitrobenzoate has m 126.5o []D (-) and (+) 25.5o (c 1.1 CHCl3), and the bis-3,5-dinitrobenzoate has m 160o []D ± 83.0o (c 1.8 CHCl3) [Wilson & Read J Chem Soc 1269 1935]. [Beilstein 6 III 4060.]
