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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 514615Generated: October 30, 2026

Triethylamine → 5-Bromomethyl-2,2-dimethyl-5-hydroxymethyl-1,3-dioxane

https://huagongshe.com/reaction/514615

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTriethylamineHCID 8471—
ReactantBicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 18462—
Reactant1,3-Propanediol, 2-(bromomethyl)-2-(hydroxymethyl)-HCID 87954—
SolventAcetoneHCID 180—
Product5-Bromomethyl-2,2-dimethyl-5-hydroxymethyl-1,3-dioxaneHCID 58165260159.8%

Reaction Conditions

Temperature25 °C

Reaction Steps

423 mg (2.13 mmol equivalents) of 2-bromomethyl-2-hydroxymethyl-1,3-propanediol was dissolved in 1.0 mL of acetone, 247 mg (1.07 mmol equivalents) of 10-camphorsulfonic acid was added thereto, and the mixture was stirred at room temperature (25° C.) for 2 days. After completion of the reaction, triethylamine was added, the solvent was removed by distillation, and the obtained crude product was then purified by silica gel column chromatography (eluent: hexane/ethyl acetate (v/v)=3/1) to give 409 mg (1.71 mmol equivalents) of 5-bromomethyl-2,2-dimethyl-5-hydroxymethyl-1,3-dioxane.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09107964B2
Source datasetuspto-grants-2015_08
ORD IDord-fc3953eb11924255a1cd5085cdbb9ce4
Source noteuspto-grants-2015_08