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Preheat the oven and prepare the cake pan: While the water infuses for 20 minutes, preheat the oven to 325°F. Brush a 9-inch round cake pan with olive oil and line the bottom with parchment paper.
Sift flour, baking soda and salt: In a large bowl, sift together flour, baking soda and salt.
Combine, hot water, chocolate and cinnamon: In a small pot, add 1/2 cup + 2 tablespoons of water and bring to a simmer. Remove pot from heat. Whisk in cocoa powder and cinnamon until smooth.
Beat eggs, oil, extracts and sugar: In a stand mixer fitted with the paddle attachment, or with a hand mixer, beat together eggs, olive oil, extracts and sugar on medium-high speed until pale yellow and ribbon-y, about 4 minutes.
Combine cocoa powder and egg mixtures: Add cocoa powder mixture to egg mixture and beat on medium-low speed until just incorporated, stopping to scrape down the sides and the bottom of the bowl. Add flour mixture and mix until just incorporated.
Bake: Pour cake batter into the prepared pan and place on the middle rack of the oven. Bake for 35-40 minutes, rotating the cake from the bottom rack to the top about halfway through the baking time. The cake is done when a tester inserted in the center comes away with only a few damp crumbs clinging to it.
Cool and Unmold the cake: Allow the cake to cool for at least 1 hour on a wire rack. Run a butter knife around the edge of the cooled cake and gently invert onto a plate. Carefully peel parchment paper off the top.
Whip the heavy cream: Using a hand mixer or in the bowl of a stand mixer fitted with the whisk attachment, whip the heavy cream, Greek yogurt and powdered sugar on medium to medium high until soft peaks form.
Serve: Slice the cake and serve with a dollop of Greek yogurt whip and some fresh berries. Serve immediately!