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1
Preheat oven to 375u00b0F. Generously butter ramekins and coat with sugar, knocking out excess. Bring large saucepan of water to boil.
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2
In small bowl, stir together 4 tablespoons butter and flour to form paste.
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3
In second small bowl, stir together Grand Marnier and simple syrup. Add cookies, tossing lightly to coat, and let soak while preparing remaining ingredients.
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4
Transfer milk to large saucepan. Split 1/2 vanilla bean lengthwise and scrape seeds into milk. Add bean. Set over moderate heat and bring to boil. Remove from heat and whisk in butter-flour mixture. Return to moderate heat and cook, whisking consistently, until thickened and smooth, about 2 minutes. Remove from heat and whisk in egg yolks and 1 egg white. Transfer souffle base to large bowl and discard vanilla bean.
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5
In second large bowl, using electric mixer, beat remaining 4 egg whites just until soft peaks form. Gradually beat in 1/2 cup sugar.
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6
Whisk 1/4 of beaten egg whites into souffle base to lighten. Gently but thoroughly fold in remaining whites.
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7
Spoon 1/2 of batter into ramekins, filling each halfway. (Alternatively, spoon batter into large pastry bag and pipe into ramekins.) Transfer 2 soaked cookies to each ramekin. Top with remaining batter. Arrange ramekins at least 1 1/2 inches apart in large baking pan and add enough hot water to pan to reach 2/3 up sides of ramekins.
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8
Bake souffles until puffed and golden, 20 to 25 minutes. Remove pan from oven and transfer ramekins to rack. Sift confectioners' sugar over, then transfer ramekins to dessert plates. With 2 forks, pull open center of each souffle and pour some creme anglaise into opening. Serve immediately.
