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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1463528Generated: October 31, 2026

Hydrochloric Acid → Methyl 1-(4'-hydroxymethylphenyl)cyclopent-3-ene-1-carboxylate

https://huagongshe.com/reaction/1463528

Reaction equation

Participants

RoleNameHCIDCharge
ReactantHydrochloric AcidHCID 313—
ReactantTetrabutylammonium FluorideHCID 2724141—
ReactantMethyl 1-(4'-t-butyldimethylsilyloxymethylphenyl)-2-vinylcyclopropane-1-carboxylateHCID 19090698—
SolventTetrahydrofuranHCID 8028—
ProductMethyl 1-(4'-hydroxymethylphenyl)cyclopent-3-ene-1-carboxylateHCID 19090695—

Reaction Steps

To a solution of the title compound of Step 2, above, (1.8 g, 5.23 mmol) in 25 ml THF was added n-Bu4NF (1.5 g, 5.75 mmol), and the resulting solution was stirred at ambient temperature for 3 hours. The mixture was poured into 50 ml 1N HCl and extracted (EtOAc, 4×30 ml). The combined extracts were dried over MgSO4, filtered and concentrated to yield 1.51 g of the title compound as an oil which was used crude in the next step.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS05300668
Source datasetuspto-grants-1994_04
ORD IDord-6539d0df347548cca7a4022e08bd4d9c
Source noteuspto-grants-1994_04