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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1753203Generated: November 1, 2026

Toluene → HCID 523407, compound

https://huagongshe.com/reaction/1753203

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTolueneHCID 1140—
ReactantChlorotrimethylsilaneHCID 6397—
Reactantdelta-GluconolactoneHCID 7027—
Reactant4-MethylmorpholineHCID 7972—
SolventWaterHCID 962—
SolventTetrahydrofuranHCID 8028—
ProductHCID 523407HCID 523407—

Reaction Conditions

Temperature17 °C

Reaction Steps

To a solution of D-(+)-glucono-1,5-lactone (21.6 kg) and N-methylmorpholine (98.2 kg) in tetrahydrofuran (192 kg) was added trimethylsilyl chloride (79.1 kg) at 40° C. or below, and then the mixture was stirred at a temperature from 30° C. to 40° C. for 4 hours. After the mixture was cooled to 17° C., toluene (93.6 kg) and water (109 kg) were added thereto. The organic layer was separated and washed with an aqueous solution of 5% sodium dihydrogen phosphate (108 kg×2) and water (108 kg×1). The solvent was evaporated under reduced pressure. To the resulting residue was added tetrahydrofuran (154 kg) and the solvent was evaporated under reduced pressure. Again tetrahydrofuran (154 kg) was added thereto and evaporated under reduced pressure. The resulting residue was dissolved in tetrahydrofuran (253 kg) to give a solution of the titled compound in tetrahydrofuran. The purity of the product was 99.0% (conversion rate: 99.1%), which was calculated based on the area ratio measured by HPLC.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09163051B2
Source datasetuspto-grants-2015_10
ORD IDord-8b228557c4054b17a8417974337dedd0
Source noteuspto-grants-2015_10