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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1580259Generated: November 2, 2026

p-Toluenesulfonic acid → dihydrospiro[cyclohexane-1,2'(1'H)-naphthalene]-4',4-dione

https://huagongshe.com/reaction/1580259

Reaction equation

Participants

RoleNameHCIDCharge
Reactantp-Toluenesulfonic acidHCID 6101—
Reactant3', 4'-dihydrospiro[cyclohexane-1,2'(1'H)-naphthalene]-4', 4-dioneHCID 12251266—
SolventBenzeneHCID 241—
Productdihydrospiro[cyclohexane-1,2'(1'H)-naphthalene]-4',4-dioneHCID 68134593—

Reaction Steps

A 3', 4'-dihydrospiro[cyclohexane-1,2'(1'H)-naphthalene]-4', 4-dione (6) obtained in step (6) is monoketalized at the non-conjugated least hindered carbonyl function, e.g., by heating (at reflux) in a solvent such as benzene with an alkylene glycol (in the presence of a catalyst such as p-toluenesulfonic acid), to yield a corresponding 3', 4', -dihydrospiro[cyclohexane-1,2'(1'H)-naphthalene]-4',4 -dione, 4-(ethylene ketal) (7).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS03932425
Source datasetuspto-grants-1976_01
ORD IDord-07cbd9b2d42443c9a221499eba3a271b
Source noteuspto-grants-1976_01