Pimelic Acid → HCID 13120336, compound

Participants

Reaction Steps

The 2-methoxy-3-[7-(4-octylphenyl)-heptyloxy]-1-propanol used as starting material is obtained in the following manner: 4-octylbenzene is reacted with the ethyl ester acid chloride of pimelic acid in the presence of aluminium chloride in nitrobenzene to give 7-(4-octylphenyl)-7-oxoheptanoic acid ethyl ester (m.p. 38°-40° C.). Subsequent hydrogenation in the presence of palladium on charcoal in ethanol with the addition of some perchloric acid gives 7-(4-octylphenyl)-heptanoic acid ethyl ester (oily substance), reduction of which with lithium aluminium hydride gives 7-(4-octylphenyl)-heptanol (oily substance). Reaction with phosphorus tribromide gives the corresponding bromide (oil) which is reacted with the monosodium salt of 2-methoxy-1,3-propandiol.

Provenance & Evidence