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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1612387Generated: November 1, 2026

Sulfuric Acid → HCID 4518867, compound

https://huagongshe.com/reaction/1612387

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSulfuric AcidHCID 1118—
Reactant826-62-0HCID 13223—
ReactantSodium borohydrideHCID 4311764—
CatalystMethanolHCID 887—
SolventTetrahydrofuranHCID 8028—
ProductHCID 4518867HCID 451886764.76%

Reaction Conditions

Temperature30 °C

Reaction Steps

Under nitrogen atmosphere, 176 g (4.649 mol) of sodium borohydride was put into a flask and 2000 g of THF and 9.8 g of methanol were added thereto. A solution of 954 g (5.812 mol) of 5-norbornene-2,3-dicarboxylic anhydride dissolved in 2800 g of THF was added thereto dropwise while cooling them by an ice bath to keep the reaction temperature at 35° C. or lower. After completion of the dropping, the mixture was stirred at 30° C. for 4 hours, then poured into 3000 g of 10% aqueous sulfuric acid solution at 20° C. or lower and stirred for a while. Under reduced pressure, THF was recovered, and 1800 g of MIBK was added thereto for extraction. Further 900 g of MIBK was added to the separated aqueous layer for extraction and combined with the organic layer. 63.6 g of sodium carbonate and 200 g of water were added to the organic layer and stirred for a while. The separated organic layer was washed with diluted sulfuric acid and water, then concentrated, thereby 565.3 g of a white solid desired product of a lactone compound was obtained (64.76% yield).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06992197B2
Source datasetuspto-grants-2006_01
ORD IDord-b890ae07178b41cdb3e1161c008e7d24
Source noteuspto-grants-2006_01