diff --git a/compiler/src/dotty/tools/dotc/core/Constants.scala b/compiler/src/dotty/tools/dotc/core/Constants.scala
index 959c677b143f..5f25dbc7d431 100644
--- a/compiler/src/dotty/tools/dotc/core/Constants.scala
+++ b/compiler/src/dotty/tools/dotc/core/Constants.scala
@@ -147,46 +147,48 @@ object Constants {
       case _         => throw new Error("value " + value + " is not a Double")
     }
 
-    /** Convert constant value to conform to given type.
-     */
-    def convertTo(pt: Type)(using Context): Constant | Null = {
-      def classBound(pt: Type): Type = pt.dealias.stripTypeVar.stripNull() match {
-        case tref: TypeRef if !tref.symbol.isClass && tref.info.exists =>
-          classBound(tref.info.bounds.lo)
-        case param: TypeParamRef =>
-          ctx.typerState.constraint.entry(param) match {
-            case TypeBounds(lo, hi) =>
-              if (hi.classSymbol.isPrimitiveValueClass) hi //constrain further with high bound
-              else classBound(lo)
-            case NoType => classBound(param.binder.paramInfos(param.paramNum).lo)
-            case inst => classBound(inst)
-          }
-        case pt => pt
-      }
-      pt match
-        case ConstantType(value) if value == this => this
-        case _: SingletonType => null
-        case _ =>
-          val target = classBound(pt).typeSymbol
-          if (target == tpe.typeSymbol)
-            this
-          else if ((target == defn.ByteClass) && isByteRange)
-            Constant(byteValue)
-          else if (target == defn.ShortClass && isShortRange)
-            Constant(shortValue)
-          else if (target == defn.CharClass && isCharRange)
-            Constant(charValue)
-          else if (target == defn.IntClass && isIntRange)
-            Constant(intValue)
-          else if (target == defn.LongClass && isLongRange)
-            Constant(longValue)
-          else if (target == defn.FloatClass && isFloatRange)
-            Constant(floatValue)
-          else if (target == defn.DoubleClass && isNumeric)
-            Constant(doubleValue)
-          else
-            null
-    }
+    import dotty.tools.dotc.core.Decorators.i
+
+    /** Convert constant value to conform to given type. */
+    def convertTo(pt: Type)(using Context): Constant | Null = pt.dealias.stripTypeVar match
+      case ConstantType(value) if value == this => this
+      case _: SingletonType => null
+      case tref: TypeRef if !tref.symbol.isClass && tref.info.exists =>
+        convertTo(tref.info.bounds.lo)
+      case param: TypeParamRef =>
+        ctx.typerState.constraint.entry(param) match
+          case TypeBounds(lo, hi) =>
+            val hiResult = convertTo(hi)
+            if hiResult != null then hiResult
+            else convertTo(lo)
+          case NoType => convertTo(param.binder.paramInfos(param.paramNum).lo)
+          case inst => convertTo(inst)
+      case pt: OrType =>
+        // For a union type, if both sides convert to constants,
+        // return a constant only if two sides convert to the same constant
+        // (same value and same tag).
+        // For example, `2` can be converted to `Byte | String | Byte`,
+        // but not to `Byte | Int` (which would be ambiguous).
+        // TODO: However, the logic will not work here, since `2: Int` is already
+        // a subtype of `Byte | Int` before `adapt`.
+        val leftResult = convertTo(pt.tp1)
+        val rightResult = convertTo(pt.tp2)
+        // println(s"convertTo OrType: $this to $pt, leftResult = $leftResult, rightResult = $rightResult, compare = ${leftResult == rightResult}")
+        if leftResult == null then rightResult
+        else if rightResult == null then leftResult
+        else if leftResult == rightResult then leftResult
+        else null
+      case pt =>
+        val target = pt.typeSymbol
+        if target == tpe.typeSymbol then this
+        else if (target == defn.ByteClass) && isByteRange then Constant(byteValue)
+        else if (target == defn.ShortClass) && isShortRange then Constant(shortValue)
+        else if (target == defn.CharClass) && isCharRange then Constant(charValue)
+        else if (target == defn.IntClass) && isIntRange then Constant(intValue)
+        else if (target == defn.LongClass) && isLongRange then Constant(longValue)
+        else if (target == defn.FloatClass) && isFloatRange then Constant(floatValue)
+        else if (target == defn.DoubleClass) && isNumeric then Constant(doubleValue)
+        else null
 
     def stringValue: String = value.toString
 
diff --git a/tests/pos/i24571.scala b/tests/pos/i24571.scala
index 7b5180acc20f..2319c3b35371 100644
--- a/tests/pos/i24571.scala
+++ b/tests/pos/i24571.scala
@@ -4,12 +4,16 @@ val n3: Int = 2
 val n4: Int | Null = 2222
 val n5: Int | Byte = 2
 val n6: Byte | Int = 10000
+val n7: 1 | Null = 1
+val n8: Byte | String = 2
 
 val x: Option[Byte] = Option(2)
 val x2: Option[Byte] = Option[Byte](2)
 val x3: Option[Int] = Option(2)
 val x4: Option[Null] = Option(null)
 val x5: Option[Byte | Null] = Option(2)
+val x6: Option[1 | Null] = Option(1)
+val x7: Option[Byte | String] = Option(2)
 
 trait MyOption[+T]
 
@@ -22,3 +26,4 @@ val test2: MyOption[Byte] = MyOption.applyOld(2)
 val test3: MyOption[Int] = MyOption(2)
 val test4: MyOption[Null] = MyOption(null)
 val test5: MyOption[Byte | Null] = MyOption(2)
+val test6: MyOption[Byte | String] = MyOption(2)