Reaction #2328976

Reaction equation

hydrochloric acid

lithium aluminum hydride

methyl trans-4-vinylcyclohexanecarboxylate

water

→

(trans-4-vinylcyclohexyl)methanol

Solvents

THF

THF

Conditions

Workup

1. 1
   workup.ADDITIONthe resulting solution was added dropwise at 15 to 16° C. over 40 minutes
2. 2
   Othera sludge-like insoluble was removed by decantation
3. 3
   Washthe resulting organic layer was washed with in turn with 10% hydrochloric acid
4. 4
   DryingThe organic layer was dried over anhydrous magnesium sulfate
5. 5
   Concentrationconcentrated

Procedure

5.7 g of lithium aluminum hydride was dispersed in 50 mL of THF and all of methyl trans-4-vinylcyclohexanecarboxylate was dissolved in 75 mL of THF and then the resulting solution was added dropwise at 15 to 16° C. over 40 minutes. After stirring at 10 to 20° C. for 30 minutes, water was slowly added. About 70 mL of 10% hydrochloric acid was added and a sludge-like insoluble was removed by decantation, and then the resulting organic layer was washed with in turn with 10% hydrochloric acid, a saturated sodium hydrogen carbonate solution, and saturated saline. The organic layer was dried over anhydrous magnesium sulfate and concentrated to obtain 26 g of (trans-4-vinylcyclohexyl)methanol.

Source