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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 (kafs4@sussex.ac.uk),
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

Procedure
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.

Data
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

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