diff --git a/codeOptimizers/src/prog8/optimizer/ExpressionSimplifier.kt b/codeOptimizers/src/prog8/optimizer/ExpressionSimplifier.kt
index e8294a4c5..2df64e661 100644
--- a/codeOptimizers/src/prog8/optimizer/ExpressionSimplifier.kt
+++ b/codeOptimizers/src/prog8/optimizer/ExpressionSimplifier.kt
@@ -54,40 +54,6 @@ class ExpressionSimplifier(private val program: Program) : AstWalker() {
         return mods
     }
 
-    override fun before(expr: PrefixExpression, parent: Node): Iterable<IAstModification> {
-        if (expr.operator == "+") {
-            // +X --> X
-            return listOf(IAstModification.ReplaceNode(expr, expr.expression, parent))
-        } else if (expr.operator == "not") {
-            when(expr.expression) {
-                is PrefixExpression -> {
-                    // NOT(NOT(...)) -> ...
-                    val pe = expr.expression as PrefixExpression
-                    if(pe.operator == "not")
-                        return listOf(IAstModification.ReplaceNode(expr, pe.expression, parent))
-                }
-                is BinaryExpression -> {
-                    // NOT (xxxx)  ->   invert the xxxx
-                    val be = expr.expression as BinaryExpression
-                    val newExpr = when (be.operator) {
-                        "<" -> BinaryExpression(be.left, ">=", be.right, be.position)
-                        ">" -> BinaryExpression(be.left, "<=", be.right, be.position)
-                        "<=" -> BinaryExpression(be.left, ">", be.right, be.position)
-                        ">=" -> BinaryExpression(be.left, "<", be.right, be.position)
-                        "==" -> BinaryExpression(be.left, "!=", be.right, be.position)
-                        "!=" -> BinaryExpression(be.left, "==", be.right, be.position)
-                        else -> null
-                    }
-
-                    if (newExpr != null)
-                        return listOf(IAstModification.ReplaceNode(expr, newExpr, parent))
-                }
-                else -> return noModifications
-            }
-        }
-        return noModifications
-    }
-
     override fun after(expr: BinaryExpression, parent: Node): Iterable<IAstModification> {
         val leftVal = expr.left.constValue(program)
         val rightVal = expr.right.constValue(program)
diff --git a/compiler/src/prog8/compiler/Compiler.kt b/compiler/src/prog8/compiler/Compiler.kt
index fbecabc74..783ff6dc5 100644
--- a/compiler/src/prog8/compiler/Compiler.kt
+++ b/compiler/src/prog8/compiler/Compiler.kt
@@ -265,10 +265,10 @@ private fun processAst(program: Program, errors: IErrorReporter, compilerOptions
     program.charLiteralsToUByteLiterals(compilerOptions.compTarget)
     program.constantFold(errors, compilerOptions.compTarget)
     errors.report()
-    program.reorderStatements(errors, compilerOptions)
-    errors.report()
     program.desugaring(errors)
     errors.report()
+    program.reorderStatements(errors, compilerOptions)
+    errors.report()
     program.addTypecasts(errors, compilerOptions)
     errors.report()
     program.variousCleanups(program, errors)
diff --git a/compiler/src/prog8/compiler/astprocessing/CodeDesugarer.kt b/compiler/src/prog8/compiler/astprocessing/CodeDesugarer.kt
index ad817ec35..e77220103 100644
--- a/compiler/src/prog8/compiler/astprocessing/CodeDesugarer.kt
+++ b/compiler/src/prog8/compiler/astprocessing/CodeDesugarer.kt
@@ -92,24 +92,25 @@ if not CONDITION
         /*
 while CONDITION { STUFF }
     ==>
-  goto _whilecond
 _whileloop:
+  if NOT CONDITION goto _after
   STUFF
-_whilecond:
-  if CONDITION goto _whileloop
+  goto _whileloop
+_after:
          */
         val pos = whileLoop.position
-        val condLabel = makeLabel("whilecond", pos)
         val loopLabel = makeLabel("whileloop", pos)
+        val afterLabel = makeLabel("afterwhile", pos)
+        val notCondition = PrefixExpression("not", whileLoop.condition, pos)
         val replacement = AnonymousScope(mutableListOf(
-            jumpLabel(condLabel),
             loopLabel,
-            whileLoop.body,
-            condLabel,
-            IfStatement(whileLoop.condition,
-                AnonymousScope(mutableListOf(jumpLabel(loopLabel)), pos),
+            IfStatement(notCondition,
+                AnonymousScope(mutableListOf(jumpLabel(afterLabel)), pos),
                 AnonymousScope(mutableListOf(), pos),
-                pos)
+                pos),
+            whileLoop.body,
+            jumpLabel(loopLabel),
+            afterLabel
         ), pos)
         return listOf(IAstModification.ReplaceNode(whileLoop, replacement, parent))
     }
diff --git a/compiler/src/prog8/compiler/astprocessing/VariousCleanups.kt b/compiler/src/prog8/compiler/astprocessing/VariousCleanups.kt
index 5b329737b..a32afa87c 100644
--- a/compiler/src/prog8/compiler/astprocessing/VariousCleanups.kt
+++ b/compiler/src/prog8/compiler/astprocessing/VariousCleanups.kt
@@ -66,4 +66,37 @@ internal class VariousCleanups(val program: Program, val errors: IErrorReporter)
 
         return noModifications
     }
+
+    override fun after(expr: PrefixExpression, parent: Node): Iterable<IAstModification> {
+        if(expr.operator=="+") {
+            // +X --> X
+            return listOf(IAstModification.ReplaceNode(expr, expr.expression, parent))
+        }
+        if(expr.operator=="not") {
+            val nestedPrefix = expr.expression as? PrefixExpression
+            if(nestedPrefix!=null && nestedPrefix.operator=="not") {
+                // NOT NOT X  -->  X
+                return listOf(IAstModification.ReplaceNode(expr, nestedPrefix.expression, parent))
+            }
+            val comparison = expr.expression as? BinaryExpression
+            if (comparison != null) {
+                // NOT COMPARISON ==> inverted COMPARISON
+                val invertedOperator =
+                    when (comparison.operator) {
+                        "==" -> "!="
+                        "!=" -> "=="
+                        "<" -> ">="
+                        ">" -> "<="
+                        "<=" -> ">"
+                        ">=" -> "<"
+                        else -> null
+                    }
+                if (invertedOperator != null) {
+                    comparison.operator = invertedOperator
+                    return listOf(IAstModification.ReplaceNode(expr, comparison, parent))
+                }
+            }
+        }
+        return noModifications
+    }
 }
diff --git a/docs/source/todo.rst b/docs/source/todo.rst
index 73c0469e7..cf9074baa 100644
--- a/docs/source/todo.rst
+++ b/docs/source/todo.rst
@@ -3,7 +3,6 @@ TODO
 
 For next compiler release (7.6)
 ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
-change desugar of while loop so that no initial jump is required
 optimize ifs containing only a jump: reuse old code from AsmGen translateComparisonExpressionWithJumpIfFalse?