Formaldehyde → 4,4-Di(hydroxymethyl)bicyclo(2.2.1)heptene

Participants

Reaction Steps

Briefly, the process of Bailey may be described as follows. Dicyclopentadiene is heated to between 240°-250° C. to form an 80-85% yield cyclopentadiene, which is allowed to react with acrolein to produce norbornene carboxaldehyde in a yield of 79% based on the cyclopentadiene (83% based on the acrolein). The resulting norbornene carboxaldehyde is allowed to react with formaldehyde and caustic to form 5-norbornene-2,2-dimethanol which is heated to between 420°-450° C. to form 1,1-dihydroxymethyl ethylene and cyclopentadiene in a yield of 10-40%. The 1,1-dihydroxymethyl ethylene, is allowed to react with dibutyl tin oxide to form a cyclic tin intermediate which is allowed to react with carbon disulfide (CS2) to form 3,9-dimethylene-1,5,7,11-tetraoxa-spiro[5,5]undecane (BMSOC).

Provenance & Evidence