Beat butter and 1 1⁄2 cups of the sugar in a large bowl with an electric mixer on low speed. Increase speed to medium; beat until light and fluffy. Add yolks one at a time, beating until smooth after each addition. Reduce speed to low and add flour 1⁄2 cup at a time, beating after each addition to combine. Scrape sides of bowl with a spatula; give the dough one last stir. Transfer dough onto a large sheet of plastic wrap and press it into a 9" × 11" rectangle. Cover with more plastic wrap, place on a large plate, and let chill for 1 hour.
Arrange racks in upper and lower thirds of oven; preheat to 325°. Divide chilled dough into 6 pieces. Rewrap 5 pieces individually in plastic wrap and chill. On a lightly floured surface, work the dough piece gently with a rolling pin to warm it slightly. Keeping surface and dough floured, roll dough into a 9" square. (If dough sticks, gently run a spatula underneath it, to release it.) Using a 3" round cookie cutter, cut out 9 circles of dough and transfer them to a parchment paper–lined baking sheet about 1" apart; reserve scraps. Repeat process with remaining chilled dough pieces. Combine leftover scraps into a ball. Reroll dough and continue cutting circles. Using a 1 1⁄4" round cookie cutter, cut a hole in the center of half of the circles—these are the tops. Bake all cookies in batches, rotating pans halfway through, until just pale golden, about 15 minutes. Let cookies cool completely.
Put preserves into a small pot and bring to a boil, stirring, over medium heat. Reduce heat to medium-low and simmer, stirring, until thickened and reduced by about one-quarter, about 5 minutes. Transfer preserves to a bowl; let cool. Put remaining 1⁄2 cup confectioners' sugar into a sieve; dust cookie tops. Turn whole cookies upside down—these are the bottoms; spoon about 1⁄2 tsp. of preserves onto each. Using a small spatula, spread preserves to within 1⁄8" of the edges. Cover each with a cookie top. Transfer remaining preserves into a plastic bag and snip the end. Using it like a piping bag, pipe a small amount of preserves into each hole. Serve cookies immediately or store between sheets of wax paper in an airtight container at room temperature.