4-Methoxyphenylacetyl chloride

Chemical Properties

clear light yellow liquid

Uses

4-Methoxyphenylacetyl chloride may be used in the synthesis of:

• substituted spiro[4.5]decane
• 1-(4′-hydroxybenzyl)-6, 7-dihydroxy-1, 2, 3, 4-tetrahydroisoquinoline (higenamine), a cardiotonic principle of aconite root
• 2,5-naphthyridine
• (R)-(+)-nor-roefractine

Synthesis

The general procedure for the synthesis of 4-methoxyphenylacetyl chloride from 4-methoxyphenylacetic acid was as follows: 16.62 g (0.1 mol) of 4-methoxyphenylacetic acid was dissolved in 10 mL of benzene, followed by the slow addition of 29 mL (0.2 mol) of thionyl chloride to the solution. The reaction mixture was heated to reflux temperature and stirred continuously for 1 hour under this condition. Upon completion of the reaction, the residual thionyl chloride in the reaction solution and the concentrated solvent were removed by distillation under reduced pressure to afford 4-methoxybenzeneacetyl chloride (Compound I) as a liquid phase product in quantitative yield. The obtained product can be used for subsequent reaction without further purification.

References

[1] European Journal of Medicinal Chemistry, 2005, vol. 40, # 8, p. 764 - 771
[2] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 22, p. 6160 - 6163
[3] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 10, p. 2899 - 2903
[4] Patent: WO2005/92896, 2005, A1. Location in patent: Page/Page column 27
[5] Chinese Chemical Letters, 2013, vol. 24, # 8, p. 673 - 676