2,4,6-Trimethylbenzoyl chloride

Aldrich ChemFiles 2007, 7.3, 6.

Aldrich ChemFiles 2007, 7.3, 6.

Whereas acid chlorides might typically be thought of as building blocks, they can also be used to protect alcohols as their corresponding esters. 2,4,6-Trimethylbenzoyl chloride is a particularly useful acid chloride in this regard, as it forms the mesitoate esters. These esters are very stable to base hydrolysis, yet can be easily cleaved reductively with LiAlH4. 1,2

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Materials

     

References

  1. Corey, E. J. et al. J. Am. Chem. Soc. 1969, 91, 4318. (b) Bolton, I. J. et al. J. Chem. Soc. C 1971, 2944.
  2. Greene, T. W.; Wuts, P. G. M. In Protective Groups in Organic Synthesis, 3rd ed.; John Wiley & Sons: New York, 1999; p.178–179.

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