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The phrase "expected that when" is grammatically correct and can be used in written English.
It is commonly used to introduce a clause that expresses an expected outcome or result. Example: It was expected that when the new law was passed, there would be a decrease in crime rates.
Exact(60)
Who expected that when the day started?
"We expected that when you come back in two weeks you will have answers to these questions," said Enright.
Bidzina Baratashvili, the station's general director, said he expected that when it began broadcasting again, it would attract public sympathy.
It is widely expected that when a turn comes, semiconductor and semiconductor equipment stocks will lead the technology sector.
"I had expected that, when he tells us how he sees the world, that he would listen to what we have to say".
It was expected that when the refinery and fertilizer plants became operational in 2019, they would create at least 235,000 jobs.
It may be expected that, when the excavation of this site is published, it will add greatly to knowledge of the Indus civilization.
Verdi fully expected that when one of his operas was performed outside Italy the libretto would be translated into the language of the audience.
I expected that, when the men came back, they would take over and bugles would sound at the end of the street and tom-toms would be beaten.
But it is expected that when copies are given to individuals named in them, the reports' substance would make its way into news accounts.
"We expected that when the army left Lebanon, Hezbollah would take over and that mobs would loot what was left behind," he said.
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Since I tried Ludwig back in 2017, I have been constantly using it in both editing and translation. Ever since, I suggest it to my translators at ProSciEditing.

Justyna Jupowicz-Kozak
CEO of Professional Science Editing for Scientists @ prosciediting.com