Method of preparing fused ring indeno compounds

A method of forming a fused ring indeno compound, which is an intermediate for preparation of a photochromic compound, wherein said fused ring indeno compound is represented by Formula (I-E),

• wherein,
• Ring-A is selected from aryl and fused ring aryl,
• n is selected from 1 to 8,
• R1 for each n is independently selected from hydrogen, hydrocarbyl and substituted hydrocarbyl each optionally and independently interrupted with at least one of —O—, —S—, —C(O)—, —C(O)O—, —S(O)—, —SO2—, —N═N—, —N(R11′)— where R11′ is selected from hydrogen, hydrocarbyl or substituted hydrocarbyl, —Si(OR8′)w(R8′)t—, where w and t are each independently selected from 0 to 2, provided that the sum of w and t is 2, and each R8′ is independently selected from hydrogen, hydrocarbyl and substituted hydrocarbyl, and combinations of two or more thereof;
• halogen;
• cyano;
• —O—R10′, or —S—R10′, or —C(O)—R10′ or —C(O)—OR10′, wherein each R10′ is independently selected from hydrogen, hydrocarbyl or substituted hydrocarbyl;
• perhalohydrocarbyl;
• and —C(O)—N(R11′)(R12′) or —N(R11′)R12′, wherein R11′ and R12′ are each independently selected from hydrogen, hydrocarbyl or substituted hydrocarbyl, or R11′ and R12′ together form a ring structure optionally including at least one heteroatom,
• R4 and R5 are each independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, halogen, —C(O)—N(R14)(R15), —N(R14)(R15), —SR16, and —OR16, where R14 and R15 are each independently selected from hydrogen, hydrocarbyl, and substituted hydrocarbyl, or R14 and R15 together form a ring, and each R16 is independently selected from hydrocarbyl and substituted hydrocarbyl,
• R6 and R7 are each independently selected from hydrogen, hydrocarbyl, and substituted hydrocarbyl, each optionally and independently interrupted with —O—, —S—, —N(R11′)—, where R11′ is selected from hydrogen, hydrocarbyl or substituted hydrocarbyl, and
• R9 is selected from —C(O)—R19 and —S(O)(O)R19, wherein R19 is selected from hydrocarbyl, and halohydrocarbyl,
• said method comprising,
• (a) in a first step, reacting together maleic anhydride and a lactone compound represented by Formula (III-A), in the presence of a catalyst, and a solvent, said solvent being substantially free of reaction with water, thereby forming an acid intermediate represented by Formula (VIII-A),
• wherein for said lactone compound represented by Formula (III-A) and for said acid intermediate represented by Formula (VIII-A), Ring-A, n, R1, R4, R5, R6, and R7 are each as described with regard to said fused ring indeno compound represented by Formula (I-E), and Y of Formula (III-A) is selected from O, S, and N(R18), where R18 is selected from hydrogen, hydrocarbyl, and substituted hydrocarbyl, and
• (b) in a second step, converting said acid intermediate represented by Formula (VIII-A) to said fused ring indeno compound represented by Formula (I-E) in the presence of a material selected from carboxylic acid halide, carboxylic acid anhydride, sulfonyl halide, sulfonyl anhydride, and combinations thereof.