Reaction #5352

Reaction equation

potassium carbonate

water

azelaic acid monomethyl ester

→

8-carbomethoxyoctan-1-ol

Solvents

tetrahydrofuran

diethyl ether

Conditions

Workup

1. 1
   workup.ADDITIONadded at such a rate as
2. 2
   Otherthe organic layer is separated
3. 3
   ExtractionThe aqueous layer is extracted three times with diethyl ether
4. 4
   WashThe combined extracts are washed with brine
5. 5
   Dryingdried over Na2SO4
6. 6
   Filtrationfiltered
7. 7
   Concentrationconcentrated in vacuo

Procedure

To a solution of 165 mL (165 mmol) of a 1.0M solution of boranetetrahydrofuran complex in tetrahydrofuran in 200 mL of dry diethyl ether at 0° C. is added dropwise 25.0 g (123 mmol) of azelaic acid monomethyl ester, added at such a rate as to prevent excessive release of gas and exothermicity. The solution is allowed to warm to room temperature overnight and is worked up by slowly adding water until gas evolution ceases. Then solid potassium carbonate is added and the organic layer is separated. The aqueous layer is extracted three times with diethyl ether. The combined extracts are washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo to give 8-carbomethoxyoctan-1-ol as a colorless oil.

Source