A Publication
of Reliable Methods
for the Preparation
of Organic Compounds
Annual Volume
Org. Synth. 1945, 25, 71
DOI: 10.15227/orgsyn.025.0071
[Sebacamic acid, methyl ester]
Submitted by W. S. Bishop
Checked by C. F. H. Allen and J. VanAllan.
1. Procedure
A. ω-Carbomethoxypelargonyl chloride. A mixture of 216 g. (1 mole) of methyl hydrogen sebacate (Note 1) and 147 g. (1.24 moles) of thionyl chloride in a 2-l. round-bottomed flask attached by a standard ground-glass joint to an upright condenser is refluxed on a steam bath for 5 hours. The condenser is then replaced by a still head having a modified side arm, and the unused thionyl chloride is removed. The residual ω-carbomethoxypelargonyl chloride is suitable for the next step. If a purer product is desired it is distilled under reduced pressure. The yield of ester chloride boiling at 158–160°/10 mm. is 194–201 g. (83–86%).
B. Methyl sebacamate. Two and one-half liters of concentrated aqueous ammonia (about 28%) in a 4-l. beaker or enameled pot (Note 2) is stirred vigorously with an off-center stirrer and chilled to 8° in a cooling bath. The crude chloride from part A is added slowly from a dropping funnel to the solution, which is kept below 8° throughout the addition. A vigorous reaction takes place, and methyl sebacamate precipitates immediately. After the addition has been completed, the product is filtered by suction and washed with 200 ml. of cold water. After 3 days' drying in a vacuum desiccator, the methyl sebacamate weighs 200–204 g. (93–95%) and melts at 72–74° (Note 3).
2. Notes
1. Methyl hydrogen sebacate (b.p. 168–170°/3 mm.) was prepared by the checkers in yields of 52–61% from sebacic acid and methanol by the procedure described for the ethyl analog.1 The ethyl ester can be used to obtain ethyl sebacamate. The preparation of the acid chloride from ethyl hydrogen sebacate is mentioned in Note 12, p. 171.
2. A variety of enameled-steel pots known as bain-marie is available from the American Specialty Company, Rochester, New York.
3. The yield is no higher with the distilled chloride.
3. Discussion
These compounds have been described in the literature.2,3
This preparation is referenced from:

References and Notes
  1. Org. Syntheses Coll. Vol. 2, 276 (1943).
  2. Biggs and Bishop, J. Am. Chem. Soc., 63, 944 (1941).
  3. Bishop, U. S. pat. 2,277,033 [C. A., 36, 4636 (1942)].

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

ammonia (7664-41-7)

methanol (67-56-1)

thionyl chloride (7719-09-7)

Ethyl hydrogen sebacate (693-55-0)

methyl hydrogen sebacate (818-88-2)

sebacic acid (111-20-6)

Methyl sebacamate,
Sebacamic acid, methyl ester (53663-35-7)

ω-Carbomethoxypelargonyl chloride

ethyl sebacamate