How to synthesise indane from Benzene ?

2018-03-02 7:35 pm

I did my synthesis, but for some reason i am unable to post the picture

1- Fridlecraft Cl-Ch2-Ch2-Cl in AlCl3
2- Mg/ether (grignard reargent)
3- Add Co2
4- Add H+
5- Benzene ring will attack the COOH
6- Reduce

My concern is step 1 and 5!

回答 (2)

胡雪8°

2018-03-03 12:36 am

Step 5 is problematic. benzene ring and -COOH group do not react.

I suggest a simple conversion as follows :

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[匿名]

2018-03-03 8:10 am

I've been teaching all day and finally have some time to respond to this question.
There is a lot of bad chemistry here.
1. Look up the structure of Indane - your proposed route seems to make a carbonyl compound. The structure shown in the other answer is correct. Indane is a hydrocarbon.
2. You cannot make indane (and nearly nothing else) by a Friedel-Crafts alkylation reaction. Alkyl groups are activating so you get polyalkylation on a few rings and nothing on all the rest.
3. I don't think dichloropropane will work - or any other poly halide in a Grignard reaction. Just too much happening at once. 1-Chloropropane will not work because it is isomerized to the isopropyl carbocation. You will get cumene [C6H5CH(CH3)2].
What are your allowed starting materials? You would like to get to C6H5CH2CH2CH2Cl and do a F-C reaction on that. Try it.

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