Reaction #927250

Reaction equation

1,1,2-Tribromo-2-(7-hydroxyheptyl)cyclopropane

Water

→

7-(1,1,2-tribromo-cyclopropyl)-heptanoic acid

Solvents

acetic acid

acetic acid

Conditions

Workup

1. 1
   workup.ADDITIONwas added
2. 2
   ExtractionThe solution was extracted with ether
3. 3
   ExtractionThe ether phase was extracted three times with 1N NaOH solution
4. 4
   workup.ADDITIONA little sodium bisulfite was added
5. 5
   Extractionextracted with ether twice
6. 6
   WashThe ether extracts were washed with brine
7. 7
   Dryingdried over magnesium sulfate

Procedure

1,1,2-Tribromo-2-(7-hydroxyheptyl)cyclopropane (0.90 g, 2.3 mmol) was dissolved in 60 ml of glacial acetic acid. A solution of 1.0 g (10 mmol) of chromium trioxide dissolved in 14 ml of 90% aqueous acetic acid was added and the reaction mixture was stirred at room temperature for 24 hours. Water (300 ml) was added. The solution was extracted with ether. The ether phase was extracted three times with 1N NaOH solution. A little sodium bisulfite was added. The aqueous extracts were acidified with 6N HCl, and extracted with ether twice. The ether extracts were washed with brine, dried over magnesium sulfate and stripped to give 0.56 g 7-(1,1,2-tribromo-cyclopropyl)-heptanoic acid.

Source