Submit a SyntheticPage About SyntheticPages Page Index Browse most recent SyntheticPages View the Leaderboard We value your feedback
  Navigation Buttons

Front Page

Log In

Join Now

Print Version


About this site

Privacy Policy

Copyright Syntheticpages ©2001

Formation of a methyl ester under acid conditions; 3-(4-methoxy-2-methoxycarbonylmethyl-6-tolyl)-propionic acid methyl ester

SyntheticPage 174 (2001)
Submitted 27th Nov 2001, published 28th Nov 2001

lisa frost (,
A contribution from the Caddick Group, Sussex

Reaction Scheme

Chemicals Used
3-(2-carboxymethyl-4-methoxy-6-tolyl)-propionic acid SP:XX Methanol (GPR) H2SO4

To a solution of the diacid (6.56 g, 26 mmol, 1 equiv) in methanol (200 mL) was added a catalytic amount of conc. H2SO4 (0.07 mL, 1.3 mmol, 5 mol%). The mixture was set to reflux for 6 h after which it was allowed to cool to room temperature. The methanol was removed in vacuo and the resulting oil washed with sat. NaHCO3 solution (20 mL). The organics were extracted into ethyl acetate (3 x 50 mL), dried (MgSO4), filtered and concentrated in vacuo leaving a brown oil which was seen to be of sufficient purity for use in further reactions. (6.32 g, 87%).

Author's Comments
This reaction is simple to carry out and is high yielding and also yields high purity material. It has been carried out on various scales, all of which have been high yielding.

1H nmr (300 MHz, CDCl3) 6.69 (1H, d, J = 2.5 Hz), 6.66 (1H, d, J = 2.5 Hz), 3.78 (3H, s), 3.72 (3H, s), 3.71 (3H, s), 3.67 (2H, s), 2.94-2.88 (2H, m), 2.45-2.37 (2H, m), 2.34 (3H, s)

Lead Reference
Rucker, Mark; Brueckner, Reinhard; Synlett.; 1997; 1187-1189.

Other References

This page has been viewed approximately 336 times since records began.

Get CDX file (Choose "Open this file from its current location" TWICE)

SyntheticPagesTM are for use exclusively by those with training and experience in synthetic chemistry. While contributors are asked to identify hazards and to use methods designed to reduce risk, no formal hazard or risk assessments are included, and these procedures must be conducted at one's own risk. SyntheticPages, its editors, owners and associates do not warrant or guarantee the safety of individuals using these procedures and hereby disclaim any liability for any injuries or damages claimed to have resulted from or related in any way to the procedures herein. Copyright ©2005 Synthetic Pages

Comment on this page!

Registered users may add comments to other pages. If you have already registered, please log in, otherwise you may register here.

Back to Top

By using this site, you agree to its Terms and Conditions