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Ester hydrolysis and methyl etherification (one pot); 1,2,4-Trimethoxybenzene

SyntheticPage 425
DOI: 10.1039/SP425
Submitted Jun 28, 2010, published Jun 28, 2010
Christopher Cooksey (rsc@chriscooksey.demon.co.uk)
A contribution from R J H Clark Group, UCL


			Reaction Scheme: Ester hydrolysis and methyl etherification (one pot)

Chemicals Used

1,2,4-triacetoxybenzene (Aldrich)
dimethyl sulfate
NaOH

Procedure

1,2,4-triacetoxybenzene (50 g, 0.198 mol) was dissolved in a mixture of methanol (100 cm3) and dimethyl sulfate (175 cm3, 1.849 mol). With mechanical stirring and ice cooling, a solution of NaOH (150 g, 3.75 mol) in water (150 cm3) was added so that the temperature remained between 25 and 30 ºC. After the addition was complete stirring was continued for a further 1 h then the mixture was allowed to stand overnight. Water (300 cm3) was added and the product was extracted with ether (4 x 100 cm3). The organic extract was dried (MgSO4), filtered,  and evaporated to give a brown oil which was distilled to give a colourless oil  bp 62-64 ºC/0.05 mm, 29.4 g (88% yield, lit: 90%). 

Author's Comments

A literature procedure worked with no problems.   This compound was prepared by the method of H D Locksley and I G Murray, J Chem Soc C, 1970, 392-398 doi:10.1039/j39700000392, which is based on that of T R Govindachari, K Nagarajan and P C Parthasarathy, J Chem Soc, 1957, 548-551 doi:10.1039/jr9570000548.

Data

δH (CDCl3, 200 MHz) 6.78d (8.7), 6.50d (2.9), 6.38dd (8.7, 2.9), 3.84s, 3.82s, 3.76s

Lead Reference

H D Locksley and I G Murray, J Chem Soc C, 1970, 392-398 doi:10.1039/j39700000392

Other References

T R Govindachari, K Nagarajan and P C Parthasarathy, J Chem Soc, 1957, 548-551 doi:10.1039/jr9570000548

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Keywords: esters, ethers, hydrolysis, methylation

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