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FOR THE CAKE:
Preheat the oven to 350 degrees F. Oil a 9-inch round cake pan. Line pan with parchment paper.
In a mixing bowl, sift together the flour, baking soda, and salt.
In the top of a double boiler set over simmering water, heat the coffee, bourbon, chocolate, and butter, stirring until the chocolate and butter are melted and the mixture is smooth. Remove the pan from the heat and stir in the sugar. Let the mixture cool for 3 minutes and transfer to an electric mixer. Add the flour mixture to the chocolate mixture, half a cup at a time, and beat medium speed for 1 minute. Add the eggs and vanilla and beat until smooth.
Pour into the prepared pan and bake for 1 1/2 hours, or until a skewer inserted in the center comes out clean. Let the cake cool completely in the pan. When cooled, turn out onto a serving plate.
FOR CHOCOLATE ICING:
Combine the chocolate and butter in the top of a double boiler and stir over low heat until they are melted and combined. Cool slightly and then ice cake.
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