Recipe: Chocolate Chip-Pineapple Upside Down Cake

by Stephanie Zonis

Chocolate Chip-Pineapple
Upside Down Cake

8 servings

It may seem an unlikely combination, but chocolate and pineapple go together very well. I have also used canned mandarin oranges (both by themselves and in combination with the pineapple rings) with great success here, and I'm sure canned pears or apricot halves would work, too; whatever you use, the fruit must be well-drained (reserve a little of the syrup/juice for the topping). The brown sugar you use must be soft and fresh. This dessert is best served warm from the oven, although I have kept it overnight and reheated it quickly in the microwave at medium power with decent results. Fun for a special brunch or tea, and great for those times when you're looking for a baking project the kids can help with.

Fruit:
5 canned pineapple rings in pineapple juice,
well-drained (reserve the
juice) OR other fruit

Optional: Pecan halves

Topping:
5 Tbsp. unsalted butter, cut into slices
1 cup firmly packed dark brown sugar
1 Tbsp. reserved pineapple juice

Cake:
1-1/2 cups all-purpose flour, divided
2 tsp. baking powder
Pinch salt
1/2 cup miniature semisweet chocolate chips
1/2 cup plus 1 Tbsp. granulated sugar
2 eggs, graded "large"
1/2 cup milk
1/3 cup corn oil

For Serving:
Lightly sweetened whipped cream
OR good vanilla ice cream

Adjust rack to center of oven; preheat oven to 350 degrees F. Use a 9 inch round layer pan for this cake, at least 1-3/4 inches deep (do not grease the pan). Slice 4 of the pineapple rings in half to make 8 half-circles. 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.

For Topping:
In 1 quart, heavy-bottomed, nonreactive pot, melt butter over low heat. Add brown sugar; increase heat to medium. Stir mixture over medium heat for 3 to 4 minutes, scraping pot sides and bottom with rubber spatula occasionally; mixture will resemble wet sand. Add pineapple juice and stir in; continue stirring just until mixture reaches a simmer. Remove from heat. Slowly pour on top of pineapple arrangement in pan bottom; topping may not cover pineapple slices entirely—OK.

For Cake:
Into medium bowl, sift together flour, baking powder, and salt. Blend well. 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.

To flour mixture in medium bowl, add sugar. In another small bowl, beat together with fork eggs and oil until well-combined; gradually beat in milk. 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 (a few small lumps left in the batter are OK). By hand, stir in chocolate chips and any remaining flour mixture with them until chips are evenly distributed.

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. 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. 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! 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). 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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