[discodermolide]

I suggested this earlier, the OP has tried it and apparently it didn't work!

[Borek]

That was just a spammer reposting earlier posts from the thread. Gone.

[darkdevil]

Try potassium carbonate in acetone at reflux.

Can anyone tell me if this works? It seems like a way to make mesityl oxide. Does that not happen?

potassium carbonate in acetone at reflux did not work for my case. However, if I change my alkyl bromide to a linear non-branched bromohexane. The reaction rate and yields are much faster. I assume the two bromine atoms next to the phenol OH and the branching of 2-ethylhexyl bromide hindered the nucleophilic attack and slowed down the reaction.

[darkdevil]

With DMF, K2CO3, KI, 2-ethylhexyl bromide and my sterically hindered phenol at 150 oC for 2 hours. The yield can is now 64%. Reaction time and temperature should be carefully controlled. If this condition is kept for 1 day, the product almost COMPLETELY disappeared.