A Publication
of Reliable Methods
for the Preparation
of Organic Compounds
Annual Volume
Org. Synth. 1956, 36, 12
DOI: 10.15227/orgsyn.036.0012
Submitted by A. T. Blomquist and Albert Goldstein1.
Checked by N. J. Leonard and F. H. Owens.
1. Procedure
A mixture of 140 g. (0.82 mole) of sebacoin (p. 840) (Note 1), 50 g. of copper chromite catalyst2 (Note 2), and 230 ml. of 95% ethanol is placed in an 800-ml. high-pressure hydrogenation bomb (Note 3). Hydrogen is admitted to the bomb at 135 atm., and the bomb is heated to 150°. When this temperature is reached, the shaker is started. The temperature is stabilized at 150° after its initial rapid fluctuation, and the hydrogenation is allowed to proceed until the mixture ceases to absorb hydrogen (2–4 hours). The heating and shaking are discontinued, and the bomb is allowed to cool to room temperature. The excess hydrogen is vented, and the bomb is dismantled.
The cis-1,2-cyclodecanediol will have crystallized out of solution, while the trans-diol remains in the ethanol. The entire mixture is washed out of the bomb with 95% ethanol (about 1 l.). The cis-glycol is redissolved by heating the ethanolic mixture at reflux temperature. Filter aid ("Celite") is added to the mixture, and the hot mixture is filtered through a bed of filter aid on a Büchner funnel to remove the catalyst. The ethanol is removed from the filtrate by distillation on a steam bath under water-pump pressure. The residue is dissolved in a minimum of hot 1:1 benzene-ethanol solution (about 250 ml.), and the cis-diol crystallizes upon cooling to room temperature. The crystals are collected by filtration, and the mother liquor is concentrated to dryness on a steam bath under water-pump pressure. The residue is again dissolved in a minimum of hot 1:1 benzene-ethanol (about 100 ml.), and additional cis-diol crystallizes upon cooling in a refrigerator. The process is repeated using 50 ml. of 1:1 benzene-ethanol solvent. The total yield of cis-1,2-cyclodecanediol is 68–73 g. (48–52%), m.p. 137–138°.
The trans-diol remains in the mother liquor and may be recovered by complete evaporation of the solvent followed by recrystallization of the residue from pentane. The yield of trans-1,2-cyclodecanediol is 38–45 g. (27–32%), m.p. 53–54°.
2. Notes
1. A sebacoin-sebacil mixture may be used.
2. A commercial catalyst was employed by the submitters: Harshaw Chemical Company, CU-0202P; 556–002.
3. A suitable apparatus is the "Aminco" high-pressure hydrogenation apparatus, manufactured by the American Instrument Company, Silver Spring, Maryland.
3. Discussion
1,2-Cyclodecanediol has been prepared by the hydrogenation of sebacoin in the presence of Raney nickel3 or platinum,4 by the reduction of sebacoin with aluminum isopropoxide4 or lithium aluminum hydride,4 and by the oxidation of cyclodecene with osmium tetroxide and pyridine.3

References and Notes
  1. Cornell University, Ithaca, New York.
  2. Org. Syntheses Coll. Vol. 2, 142 (1943), Note 11.
  3. Prelog, Schenker, and Günthard, Helv. Chim. Acta, 35, 1598 (1952); Prelog, Urech, Bothner-By, and Würsch, Helv. Chim. Acta, 38, 1095 (1955).
  4. Blomquist, Burge, and Sucsy, J. Am. Chem. Soc., 74, 3636 (1952).

Chemical Abstracts Nomenclature (Collective Index Number);
(Registry Number)


ethanol (64-17-5)

hydrogen (1333-74-0)

platinum (7440-06-4)

nickel (7440-02-0)

pyridine (110-86-1)

aluminum isopropoxide

Pentane (109-66-0)

benzene-ethanol (60-12-8)


lithium aluminum hydride (16853-85-3)

osmium tetroxide (20816-12-0)

1,2-Cyclodecanediol (21014-77-7)