Preparation Preheat oven to 375°F. Generously butter ramekins and coat with sugar, knocking out excess. Bring large saucepan of water to boil. In small bowl, stir together 4 tablespoons butter and flour to form paste. In second small bowl, stir together Grand Marnier and simple syrup. Add cookies, tossing lightly to coat, and let soak while preparing remaining ingredients. 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 soufflé base to large bowl and discard vanilla bean. In second large bowl, using electric mixer, beat remaining 4 egg whites just until soft peaks form. Gradually beat in 1/2 cup sugar. Whisk 1/4 of beaten egg whites into soufflé base to lighten. Gently but thoroughly fold in remaining whites. 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. Bake soufflés 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 soufflé and pour some crème anglaise into opening. Serve immediately.
Preparation Preheat oven to 375°F. Generously butter ramekins and coat with sugar, knocking out excess. Bring large saucepan of water to boil. In small bowl, stir together 4 tablespoons butter and flour to form paste. In second small bowl, stir together Grand Marnier and simple syrup. Add cookies, tossing lightly to coat, and let soak while preparing remaining ingredients. 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 soufflé base to large bowl and discard vanilla bean. In second large bowl, using electric mixer, beat remaining 4 egg whites just until soft peaks form. Gradually beat in 1/2 cup sugar. Whisk 1/4 of beaten egg whites into soufflé base to lighten. Gently but thoroughly fold in remaining whites. 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. Bake soufflés 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 soufflé and pour some crème anglaise into opening. Serve immediately.