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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 914488Generated: October 30, 2026

Cyclohexanone → 1,5-Dioxaspiro[5.5]undecane

https://huagongshe.com/reaction/914488

Reaction equation

Participants

RoleNameHCIDCharge
ReactantCyclohexanoneHCID 7967—
Reactant1,3-PropanediolHCID 10442—
Catalystp-Toluenesulfonic acid monohydrateHCID 521998—
SolventTolueneHCID 1140—
Product1,5-Dioxaspiro[5.5]undecaneHCID 909698.1%

Reaction Steps

Cyclohexanone (7.94 g) was dissolved in toluene (200 mL), 1,3-propanediol (12.3 g) and p-toluenesulfonic acid monohydrate (0.1 g) were added thereto, and the mixture was heated under reflux for 1.5 hr while removing water being produced. The temperature was allowed to cool to room temperature, and the mixture was washed with saturated aqueous sodium hydrogen carbonate solution and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give the title compound (12.4 g) as a colorless oil.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08026370B2
Source datasetuspto-grants-2011_09
ORD IDord-6593f7c6d8b141bab5a085b90fa7696d
Source noteuspto-grants-2011_09