Jan. 13,  2011  89  US 2011/0008728 Al  [Chemical Formula 109]  Compound (VI)  0 ~:  WW  0  Ha  Ha  Ha  H  O’SD  Acid generator (B13)  [Chemical Formula 111]  [Chemical Formula 11 OJ  Compound (VI)  Compound (IV)  [1161]  The obtained acid generator (B13) was analyzed by  NMR.  [1162]  $^{1}$H-NMR (DMSO-d6, 400 MHz):  Ii  (ppm)=7.76-7.  88 (m, !OH, Phenyl), 7.62 (s, 2H, Phenyl), 4.64 (s, 2H, H 6 ),  4.43-4.44 (t, 2H, ff), 4.22-4.23 (t, 2H,  Hd),  1.51-2.36 (m,  38H, Adamantane+Ha+Hc)  [1163]  $^{19}$F-NMR (DMSO-d6, 376 MHz):  Ii  (ppm)=-106.7  [1164]  From the results shown above, it was confirmed that  the acid generator (B13) had a structure shown below.  [1159]  (iv) Synthesis of Acid Generator (B13)  [1160]  4.77 g of the compound (VI) was dissolved in 23.83  g of dichloromethane and 23.83 g of pure water, and 3.22 g of  the compound (IV) was then added to the resulting solution.  The resultant was stirred for 1 hour, followed by liquid sepa› ration to collect the organic phase. The organic phase was  washed with 3.84 g of water three times. Thereafter, the  resulting organic layer was concentrated and solidified,  thereby obtaining 4.98 g ofa compound (B13) (yield: 87%).  Acid-Generator Synthesis Example 5  Synthesis of Acid Generator (B14)  [1165]  (i) Synthesis of Compound (5)  [1166]  4.74 gofxylenol and 16.1 gofanhydrouspotassium  carbonate were mixed in 94.8 g of acetone. Then, 32.9 g of  1-iodohexane was gradually added thereto in dropwise man› ner, and a reaction was effected for 19 hours under reflux.  After the reaction, the reaction mixture was cooled and sub› jected to filtration. Acetone was removed from the obtained  filtrate, thereby obtaining 25.5 g of a viscous liquid. Then,  25.4 g of t-butylmethylether and 25.4 g of a 1 % aqueous  solution of sodium hydroxide were added to the obtained  liquid, and the organic phase was collected, followed by  washing the organic phase with 25 .4 g of a 1 % aqueous  solution of sodium hydroxide. The organic phase was col› lected again, and washing was conducted four times with 25 .4  g of a 1 % aqueous solution of sodium hydroxide. Thereafter,  t-butylmethylether was removed to obtain 23.5 g of a crude  product. 