Cinnamaldehyde diacetate

A brief exposure of diacetate derivatives of aromatic aldehydes to MW irradiation on neutral alumina surface rapidly regenerates aldehydes (Scheme 6.5) [36], The selectivity in these deprotection reactions is achievable by merely adjusting the time of irradiation. As an example, for molecules bearing acetoxy functionality (R = OAc), the aldehyde diacetate is selectively removed in 30 s, whereas an extended period of 2 min is required to cleave both the diacetate and ester groups. The yields obtained are better than those possible by conventional heating methods and the procedure is applicable to compounds bearing olefmic moieties such as cinnamaldehyde diacetate [36],... 

Cinnamaldehyde diacetate was reduced by heating at 100° with iron in 50% acetic acid to cinnamyl acetate in 60.7% yield [800]. 

Also, o-nitrodnnamaldehyde may be prepared by nitration of cinnamaldehyde diacetate with acetyl nitrate [223]. Regeneration of the aldehyde group is conveniently done by mild hydrolysis with Phillips Milk of Magnesia (Loewenthal, unpubl.). 

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