Citronellol → Citronellic acid

Participants

Reaction Steps

Citronellol is oxidized with a chromate-type oxidizing agent (e.g., Jones reagent) to the carboxylic acid which is then esterified to give an ester of citronellic acid. The double bond is converted into an epoxide by a peroxide as described in Step 4. And then, the epoxide is oxidatively cleaved with a periodate to give an aldehyde, which is converted into the olefinic compound by convention Wittig reaction using trimethylphosphonium bromide and a base. The compound thus prepared is condensed with dimethyl methylphosphonate in the presence of base to give the desired compound. When an optically active compound such as (S)-(-)-citronellol is used as a starting material and allowed to react in the same manner, (S)-dimethyl 2-oxo-4-methyl-7-octenylphosphonate is prepared.

Provenance & Evidence