Patent ID: 8765978

Claim:
A method of making an indeno-fused naphthopyran represented by the following Formula XI, wherein, m and n are each independently selected from 0 to 4, R 1 for each m is halogen or R 10′ , wherein R 10′ is hydrogen, R 2 for each n is independently hydrocarbyl optionally interrupted with at least one of —O—, or —S—, and combinations thereof; substituted hydrocarbyl interrupted with at least one of —O—, or —S—, and combinations thereof; halogen; —O—R 10 ′, wherein each R 10 ′ is independently selected from hydrogen, hydrocarbyl or substituted hydrocarbyl, R g and R h are each independently hydrogen or hydrocarbyl, and B and B′ are each independently selected from unsubstituted aryl, substituted aryl, unsubstituted heteroaryl, substituted heteroaryl, B and B′ taken together form a ring structure selected from unsubstituted fluoren-9-ylidene, substituted fluoren-9-ylidene, saturated spiro-monocyclic hydrocarbon ring, saturated spiro-bicyclic hydrocarbon ring, and spiro-tricyclic hydrocarbon ring, said method comprising, (a) reacting an alkyl benzene represented by Formula II with maleic anhydride in the presence of a bishydrocarbyl peroxide represented by the formula R a —O—O—R b , where R a and R b are each independently hydrocarbyl or substituted hydrocarbyl, thereby forming a succinic acid substituted intermediate represented by Formula III, (b) converting the succinic acid substituted intermediate represented by Formula III to a succinic anhydride substituted intermediate represented by Formula IV, (c) converting the succinic anhydride substituted intermediate represented by Formula IV to an indanone acid intermediate represented by Formula V, (d) reacting the indanone acid intermediate represented by Formula V with a nucleophile represented by Formula VI to form a substituted indanone intermediate represented by at least one of Formula VIIa, Formula VIIb and Formula VIIc, wherein M represents a counterion comprising a metal selected from Mg, Li, Cu and combinations thereof, (e) converting said substituted indanone intermediate represented by at least one of Formula VIIa, Formula VIIb and Formula VIIc to an indeno-fused naphthol represented by Formula I, and (f) reacting the indeno-fused naphthol represented by Formula I with a propargyl alcohol represented by Formula XII thereby forming said indeno-fused naphthopyran represented by Formula XI,