Synthesis of Example 1 Chromophore from WO2021263164A1: Nonlinear optical chromophores comprising a diamondoid group Example 1a: Synthesis of 1- ( 4 - methoxyphenyl ) -2,2,4,7 - tetram ethyl - 3,4 - dihydroquinol Raws CAS Solids Mass (g) Lab Scale Pricing ($/Kg) Commercial Source Pricing ($/Kg) Source 1,2,3,4-Tetrahydro-2,2,4,7-tetramethylquinoline 59388-58-8 10 6000 1608 Molecules PDF (matrix-fine-chemicals.com) 4-Bromobenzyl methyl ether 1515-88-4 11.9 23300 16800 4-Bromobenzyl methyl ether, 98% | 1515-88-4 | J&K Scientific - J&K Scientific LLC (jk-sci.com) Pd(OAc)2 3375-31-3 0.593 70000 70000 Palladium(II) acetate reagent grade, 98 3375-31-3 (sigmaaldrich.com) potassium tert butoxide 865-47-4 7.71 158 158 Potassium tert-butoxide, 98+%, pure, Thermo Scientific | Fisher Scientific Total Product 14.5 26206.77103 17843.32276 Total Product Account For 87.3% yield 1270 33282.59921 22661.0199 Example 1b. Synthesis of l-(4-methoxyphenyl)-2,2,4,7-tetramethyl- 3,4-dihydroquinoline-6-carbaldehyde Raws CAS Solids Mass (g) Lab Scale Pricing ($/Kg) Commercial Source Pricing ($/Kg) Source 1 -(4-methoxypheny 1 )-2,2 ,4,7 -tetramethyl-3 ,4- dihydroquinoline 10.9 10879 Patent POCl3 7.92 105 70 Phosphorus(V) oxychloride ReagentPlus � , 99 10025-87-3 (sigmaaldrich.com), https://dir.indiamart.com/impcat/phosphorus-oxychloride.html Total Product 10.6 11239.19811 Total Product Account for 94.3% yield 1060 11913.55 Example 1c. Synthesis of 2-(l-adamantylsulfanyl)-3,5,5-trimethyl- cyclohex-2-en- 1 -one Raws CAS Solids Mass (g) Lab Scale Pricing ($/Kg) Commercial Source Pricing ($/Kg) Source 4,4,6-trimethyl-7-oxabicyclo[4.1.0]heptan-2-one 10276-21-8 39 6760 Isophorone Oxide 10276-21-8 | TCI AMERICA (tcichemicals.com) Sodium Ethoxide 141-52-6 23.6 106 Sodium Ethoxide 141-52-6 | TCI AMERICA (tcichemicals.com) Adamantane-1-thiol 34301-54-7 44.8 26200 1-Adamantanethiol 95 34301-54-7 (sigmaaldrich.com) Total Product 73.9 15916.9364 Total Product Account for 95.9% yield 1043 16601.36467 Example 1d. Synthesis of 2-( 1 -adamantylsulfanyl)-3-[(E)-2-[ 1 -(4- methoxyphenyl)-3,4-dihydro-2H-quinolin-6-yl]vinyl]-5,5-dimethyl-cyclohex-2-en-l- one Raws CAS Solids Mass (g) Lab Scale Pricing ($/Kg) Commercial Source Pricing ($/Kg) Source l-(4-methoxyphenyl)-2,2,4,7-tetramethyl-3,4- dihydroquinoline-6-carbaldehyde 5 6710 Patent 2-( 1 -adamantylsulfanyl)- 3,5,5-trimethyl-cyclohex-2-en-l-one 4.94 11423 Patent Lithium Ethoxide (95%) 0.212 13220 Lithium ethoxide 95 2388-07-0 (sigmaaldrich.com) Piperidine 1.53 150 Piperidine ReagentPlus, 99 110-89-4 (sigmaaldrich.com) Total Product 7.09 8354.338505 Total Product Account for 74.4% yield 1344 11228.23095 Example 1e. Synthesis of (2E)-2-[2-(l-adamantylsulfanyl)-3-[(E)-2- [l-(4-methoxyphenyl)-2,2,4,7-tetramethyl-3,4-dihydroquinolin-6-yl]vinyl]-5,5- dimethyl-cyclohex-2-en- 1 -ylidene]acetonitrile Raws CAS Solids Mass (g) Lab Scale Pricing ($/Kg) Commercial Source Pricing ($/Kg) Source 2-( 1 - adamantylsulfanyl)-3-[(E)-2-[l-(4-methoxyphenyl)-2,2,4,7-tetramethyl-3,4- dihydroquinolin-6-yl] vinyl] -5,5-dimethyl-cyclohex-2-en- 1 -one 5 6814.6 Patent n-BuLi 109-72-8 25.4 100.55 n-Butyllithium 2.5M hexanes 109-72-8 (sigmaaldrich.com) Total Product 4.78 7662.546025 Total Product Account for 90.7% yield 1102 8444.12572 Example 1f. Synthesis of (2E)-2-[2-(l-adamantylsulfanyl)-3-[(E)-2- [l-(4-methoxyphenyl)-2,2,4,7-tetramethyl-3,4-dihydroquinolin-6-yl]vinyl]-5,5- dimethyl-cyclohex-2-en- 1 -ylidene]acetaldehyde Raws CAS Solids Mass (g) Lab Scale Pricing ($/Kg) Commercial Source Pricing ($/Kg) Source (2E)-2-[2-(l-adamantylsulfanyl)-3-[(E)-2-[l-(4- methoxyphenyl)-2, 2, 4, 7-tetramethyl-3,4-dihydroquinolin-6-yl]vinyl]-5, 5-dimethyl- cyclohex-2-en- 1 -ylidene]acetonitrile 17.3 10298.46 Patent DIBAL 38.2 876 Diisobutylaluminum hydride reagent grade 1191-15-7 (sigmaaldrich.com) Total Product 10.4 20348.7075 Total Product Account for 79.8% yield 1253 25496.9305 Example 1g. Synthesis of 2-[4-[(E,3E)-3-[2-(l-adamantylsulfanyl)-3- [(E)-2-[l-(4-methoxyphenyl)-2,2,4,7-tetramethyl-3,4-dihydroquinolin-6-yl]vinyl]-5,5- dimethyl-cyclohex-2-en- 1 -ylidene]prop- 1 -eny l]-3-cyano-5-phenyl-5- (trifluoromethyl)-2-furylidene]propanedinitrile Raws CAS Solids Mass (g) Lab Scale Pricing ($/Kg) Commercial Source Pricing ($/Kg) Source (2E)-2-[2-( 1 -adamantylsulfanyl)-3- [(E)-2-[l-(4-methoxyphenyl)-2,2,4,7-tetramethyl-3,4-dihydroquinolin-6-yl]vinyl]-5,5- dimethyl-cyclohex-2-en- 1 -ylidene]acetaldehyde 9.52 25497 Patent 2- [3-cyano-4-methyl-5-phenyl-5-(trifluoromethyl)-2-furylidene]propanedinitrile 436097-14-2 4.99 154000 https://www.ambeed.com/products/436097-14-2.html Total Product 6.93 145915.0707 Total Product Account for 51.7% yield 1934 282199.7467 Example 1 Chromophore $282200/kg