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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1874776Generated: October 31, 2026

Ethyl Acetate → 3-Chloro-5-hydroxybenzonitrile

https://huagongshe.com/reaction/1874776

Reaction equation

Participants

RoleNameHCIDCharge
ReactantEthyl AcetateHCID 8857—
ReactantLithium ChlorideHCID 433294—
Reactant3-Chloro-5-methoxybenzonitrileHCID 21949921—
SolventDimethylformamideHCID 6228—
Product3-Chloro-5-hydroxybenzonitrileHCID 2194987884.7%

Reaction Conditions

Temperature180 °C

Reaction Steps

To a stirred solution of LiCl (84 g, 1980 mmol) in DMF (500 mL) was added 3-chloro-5-(methyloxy)benzonitrile (167 g, 1000 mmol). The reaction mixture was heated to 180° C. for 12 h. The reaction mixture was poured into ice (300 g) and EtOAc was added. The organic layer was separated, dried over MgSO4 and evaporated to dryness. The solid was recrystallized from EtOAc and petroleum ether (1:5) to afford the title compound (130 g, 67%) as a solid.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08304419B2
Source datasetuspto-grants-2012_11
ORD IDord-2a62b91b727145e599f9247d2683759e
Source noteuspto-grants-2012_11