Chocolate Chip Pineapple Upside Down Cake

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Chocolate Chip Pineapple Upside Down Cake

Add something to your pineapple upside down cake recipe that will make it unforgettable - chocolate chips! This ooey-gooey chocolaty delight is baked to perfection with a glazed sugary top. Having just one slice seems impossible.

Ingredients

  • 5 canned pineapple rings in juice, well-drained (reserve juice)
  • pecan halves, optional
  • 5 tablespoons unsalted butter, cut into slices
  • 1 cup firmly packed dark brown sugar
  • 1 tablespoon reserved pineapple juice
  • 1 1/2 cup all-purpose flour, divided
  • 2 teaspoons baking powder
  • pinch salt
  • 1/2 cup miniature semisweet chocolate chips
  • 1/2 cup plus 1 tablespoon of granulated sugar
  • 2 eggs, graded
  • 1/2 cup milk
  • 1/3 cup corn oil

Instructions

  1. Adjust rack to center of oven; preheat oven to 350 degrees F.
     
  2. Use a 9-inch round layer pan for this cake, at least 1-3/4 inches deep (do not grease the pan).
     
  3. Slice 4 of the pineapple rings in half to make 8 half-circles.
     
  4. Place the whole pineapple slice in the center of the pan, then place the 8 half-circles pinwheel-fashion around the whole slice. If desired, place some pecan halves between the "spokes" of the pinwheel, flat sides up.
     
  5. In 1 quart, heavy-bottomed, nonreactive pot, melt butter over low heat. Add brown sugar; increase heat to medium.
     
  6. Stir mixture over medium heat for 3 to 4 minutes, scraping pot sides and bottom with rubber spatula occasionally; mixture will resemble wet sand.
     
  7. Add pineapple juice and stir in; continue stirring just until mixture reaches a simmer. Remove from heat.
  8. Slowly pour on top of pineapple arrangement in pan bottom; topping may not cover pineapple slices entirely.
     
  9. Into medium bowl, sift together flour, baking powder, and salt. Blend well.
     
  10. Remove about a tablespoon (no need to measure) to a small bowl; add chocolate chips and stir well to coat with flour mixture. Set chips aside.
     
  11. Add sugar to flour mixture in medium bowl.
     
  12. In another small bowl, beat together with fork eggs and oil until well-combined; gradually beat in milk.
     
  13. All at once, add liquid ingredients to dry ingredients. With whisk or hand-held mixer on a low speed, beat batter just until well-combined, about 30 to 60 seconds, scraping bottom and sides of bowl with rubber spatula.
     
  14. By hand, stir in chocolate chips and any remaining flour mixture with them until chips are evenly distributed.
     
  15. By small spoonfuls, place batter on top of topping and fruit in pan, making it as even a layer as possible. Bake in preheated oven about 25 to 30 minutes.
     
  16. Top of cake will be a light golden brown, and you may see some cracks in the top of the cake as well. Test for doneness by pressing top center of cake lightly with fingertip; if cake springs back, it's done. Do not overbake.
     
  17. Remove to cooling rack; allow to stand 10 to 15 minutes. Make sure your serving plate has shallow sides and a flat center portion at least 9-1/2 inches in diameter!
     
  18. Invert serving plate on top of cake, then carefully turn whole assembly over. Allow inverted cake pan to stand 1 or 2 minutes, then remove carefully (it's still hot).
     
  19. You'll have a chocolate chip cake layer topped with a caramel-like thick syrup and a pattern of pineapple slices over all. Serve slices warm, perhaps with a bit of lightly sweetened whipped cream or a scoop of vanilla ice cream.

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