Chocolate Orange Upside Down Cake

January 26, 2010
1 Ratings
  • Serves 1 9 inch cake
Author Notes

I found an old cookbook of my mother's today while I was cleaning out some bookshelves. It is called LOYALTY COOK BOOK which was published by The Native Daughters of the Golden West(Santa Rosa Parlor#217) in 1940. The recipe for cake uses no eggs and contains vinegar as an ingredient for a chocolate cake! I just had to try it, but I changed a few specs and here it is. I have always loved pineapple upside down cake and this recipe was for chocolate pineapple upside down cake which sounded a little unusual...I decided that orange would be better. I was also pleasantly surprised at how moist the cake was. (I am always nervous when I change a lot of things when baking so I made this 4 times with consistant results...whew!) —dymnyno

What You'll Need
  • 2 tbs butter
  • 3/4 cup brown sugar
  • 1 tsp instant coffee (dry)
  • 2 thinly sliced oranges
  • 1 cup sugar for cooking oranges
  • 1/4 cup butter(softened)
  • 1 1/2 cups sugar
  • 2 cups flour
  • 1/4 cup ground cocoa (like guittard)
  • 1 tsp baking soda
  • 1 1/2 cups milk
  • 1 tsp cointreau or French 44(made from orange and coffee beans)
  • 2 tbs white vinegar
  1. In a nonstick shallow pan melt 2 tbs butter and mix in the instant coffee and then spread the brown sugar evenly over the pan. (used a 9 inch pan)
  2. Very thinly slice the oranges and simmer them in water for about 6 minutes. Drain and then add 1 cup of sugar and 1 cup of water , return the oranges to the pan and cook for about 10 to 15 minutes until the sugar thickens. Remove the orange slices and arrange them on the brown sugar and butter and coffee. Drizzle some of the thick sugar from the sugared orange step over the arranged oranges.
  3. Cream the butter and the sugar. Sift the flour with the ground chocolate and soda and add to the butter and sugar and alternately with the milk. Add the cointreau (or French 44) and beat well. Finally , add the vinegar and beat again..
  4. Pour into the pan over the oranges and bake in a 350 degree oven for about 30 to 40 minutes. (Do not overfill the pan...the mixture rises and will overflow if you put too much in the pan.
  5. Remove...wait a few minutes and invert the pan onto a plate so the oranges are on the top.
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3 Reviews

Jennine June 19, 2018
I was so glad to find this recipe. I am going to add Chocolate Orange Balsanic Vinegar and enter it in this years 2018 State Fair. Did not know there were Native Daughter's of the Golden West cookbooks. My mother was president of the Oakland group in 1936. Instead of being in the parade in Oakland that year she was having me by c section. She said if she could not be in the parade that day she would have a baby instesd
EmilyNunn January 28, 2010
I like!
gabrielaskitchen January 27, 2010
oh wow, great idea! Recipes like this one make me think, "why even try!" Yum, will definitely be making this cake soon!