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1
Preheat the oven to 400F.
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2
Butter a 10-inch nonstick Bundt pan (12-cup capacity).
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3
To make the caramel, stir together the granulated sugar and 1/4 cup water in a large heavy saucepan set over medium-high heat.
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4
Cook, brushing down the sides of the pan with a wet pastry brush to prevent crystals from forming, until the sugar melts and the mixture becomes a dark amber caramel.
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5
Working quickly and carefully, immediately pour the hot caramel into the prepared Bundt pan, tilting it to cover the bottom and halfway up the sides of the pan.
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6
Let the caramel cool completely for 4 hours or overnight in the refrigerator.
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7
Place the caramel-coated Bundt pan in a roasting pan, and fill the roasting pan halfway with water.
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8
To make the chocolate cake, whisk the boiling water and the cocoa powder in a medium bowl to blend.
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9
Whisk in the milk and the vanilla extract.
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10
In another medium bowl, whisk the flour, baking soda, and salt together.
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11
Using an electric mixer, beat together the butter, brown sugar, and granulated sugar until the mixture is pale and fluffy.
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12
Add the eggs, one at a time, beating well after each addition.
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13
Mix in the flour and cocoa mixtures alternately in batches, beginning and ending with the flour (the batter may separate; do not worry).
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14
Pour the batter into the Bundt pan.
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15
To make the flan, combine the evaporated milk, condensed milk, eggs, and vanilla in a blender.
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16
Blend for 30 seconds on high speed, until smooth.
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17
Pour the mixture gently over the chocolate batter in the Bundt pan.
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18
Cover the pan with foil, and carefully transfer it, in the water-filled roasting pan, to the oven.
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19
Bake for 15 minutes.
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20
Reduce the oven temperature to 350F, and continue baking until a tester inserted into the cake comes out clean, about 1 hour.
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21
Let the cake cool in the pan for 15 minutes.
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22
Then carefully run a small knife around the edge of the cake, and invert the cake onto a platter.
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23
Cool for 1 hour.
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24
Cover, and refrigerate overnight.
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25
Serve chilled.
