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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1695234Generated: October 25, 2026

Hydrochloric Acid → 4-(1-Methylethoxy)-beta-oxobenzenepropanenitrile

https://huagongshe.com/reaction/1695234

Reaction equation

Participants

RoleNameHCIDCharge
ReactantHydrochloric AcidHCID 313—
ReactantAcetonitrileHCID 6342—
ReactantSodium hydrideHCID 24758—
ReactantMethyl 4-(1-methylethoxy)benzoateHCID 3015807—
SolventTolueneHCID 1140—
Product4-(1-Methylethoxy)-beta-oxobenzenepropanenitrileHCID 20387514—

Reaction Conditions

Temperature80 °C

Reaction Steps

To a solution of 4-Isopropoxy-benzoic acid methyl ester (2.2 g, 11.2 mmol, 1.0 eq) in dry toluene (15 mL) under N2, NaH (50-60% dispersion in mineral oil, 1.1 g, 22.4 mmol, 2.0 eq) was added. The mixture was heated at 80° C. and then dry CH3CN was added dropwise (2.8 mL, 56.0 mmol, 5.0 eq). The reaction was heated for 18 hours, then was allowed to cool down to room temperature and acidified with HCl 2N. The organic phase was recovered and 2.0 g of crude were obtained and it was used for cyclization without further purification.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08163729B2
Source datasetuspto-grants-2012_04
ORD IDord-009cc470c01b4f7bba83b356848fb8bf
Source noteuspto-grants-2012_04