ChemicalBook CAS DataBase List (1R,3S)-(-)-CAMPHORIC ANHYDRIDE

(1R,3S)-(-)-CAMPHORIC ANHYDRIDE synthesis

5synthesis methods

Product Name:(1R,3S)-(-)-CAMPHORIC ANHYDRIDE
CAS Number:595-29-9
Molecular formula:C10H14O3
Molecular Weight:182.22

124-83-4 Synthesis

124-83-4
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595-29-9
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Yield:595-29-9 95%

Reaction Conditions:

with thionyl chloride;sodium carbonate in 1,4-dioxane;dichloromethane;Reflux;

Steps:

(1R,5S)-1,8,8-Trimethyl-3-oxabicyclo[3.2.1]octane-2,4-dione (2) was synthesized by a known method.²² Finelypowdered Na2CO3 (4.24 g, 40 mmol,) was mixed with thefreshly distilled SOCl2 (3 ml, 40 mmol, ρ 1.63 g/ml) in a250-ml round-bottom flask at room temperature. To theresulting powder, a solution of carboxylic acid 1 (8.00 g,40 mmol,) in a 1:1 mixture of anhydrous CH2Cl2/dioxane(150 ml) was slowly added. The resulting solution wasrefluxed. The progress of the reaction was followed by TLCuntil no starting material could be detected. After coolingto ambient temperature, the product was then filtered andthe residue was washed thoroughly with CH2Cl2 (100 ml).Evaporation of the solvent under reduced pressurefurnished the desired anhydride, yield 6.92 g (95%).

References:

Chernyshov, Vladimir V.;Yarovaya, Olga I.;Peshkov, Roman Yu.;Salakhutdinov, Nariman F. [Chemistry of Heterocyclic Compounds,2020,vol. 56,# 6,p. 763 - 768][Khim. Geterotsikl. Soedin.,2020,vol. 56,# 8,p. 763 - 768,6]