Isopropanol → Ethyl 3-(5-chloro-2-methoxyphenyl)-2-cyanoacrylate

HRID 554818Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH3:11])=[C:6]([CH:9]=1)[CH:7]=O.[C:12]([O:15][CH2:16][CH2:17][C:18]#[N:19])(=O)[CH3:13].C([OH:23])(C)C>[Cl-].C([N+](CC)(CC)CC1C=CC=CC=1)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH3:11])=[C:6]([CH:7]=[C:17]([C:18]#[N:19])[C:16]([O:15][CH2:12][CH3:13])=[O:23])[CH:9]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 5-chloro-2-methoxybenzaldehyde (32.2 g), cyanoethyl acetate and triethylbenzyl ammonium chloride (8.6 g) was stirred at 80° C. for 7 hours. To the reaction solution, isopropyl alcohol (97 ml) was added, then the mixture was stirred under ice cooling for 1 hour. The precipitated crystals were collected by filtration and dried in vacuo to obtain the title compound in an amount of 42.7 g as crystals.

Workup

stirringthe mixture was stirred under ice cooling for 1 hour
filtrationThe precipitated crystals were collected by filtration
customdried in vacuo

Sources & evidence

ORD record: ord-f325eca91b844936a50392e4b074a390
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08049006B2

Reaction notes

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