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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1885749Generated: October 25, 2026

4-Cyanophenol → 2,2-dimethyl-2H-1-benzopyran-6-carbonitrile

https://huagongshe.com/reaction/1885749

Reaction equation

Participants

RoleNameHCIDCharge
Reactant4-CyanophenolHCID 13019—
Reactant1-Butyne, 3-chloro-3-methyl-HCID 70679—
SolventPropargyl etherHCID 23349—
Product2,2-dimethyl-2H-1-benzopyran-6-carbonitrileHCID 2779074—

Reaction Steps

According to EPO 0 076 075 describing the possibilities for preparing Kromakalim 4-cyano-phenol of the formula (I) ##STR4## is reacted with 3-chloro-3-methyl-butyne resulting in propargyl-ether of the formula (IX) ##STR5## which is then subjected to ring closure to produce 6-cyano-2,2-dimethyl-2H-1-benzopyran of the formula (III) ##STR6## The compound of the formula (III) is then converted through 6-cyano-trans-3-bromo-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-4-ol to 6-cyano-3,4-dihydro-3,4-epoxy-2,2-dimethyl-2H-1-benzopyran of the formula (V). ##STR7## From the compound of the formula (V) the end-product of the formula (VI) can be obtained by three independent routes.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS05145985
Source datasetuspto-grants-1992_09
ORD IDord-88f13fcc82b9429998671f5d129e5036
Source noteuspto-grants-1992_09