Reacción #2328976

ord-ddc890fef2474e41b5f817a96d24f359

Ecuación de reacción

Cl
hydrochloric acid
[Al+3].[H-].[H-].[H-].[H-].[Li+]
lithium aluminum hydride
C=C[C@H]1CC[C@H](C(=O)OC)CC1
methyl trans-4-vinylcyclohexanecarboxylate
O
water
C=C[C@H]1CC[C@H](CO)CC1
(trans-4-vinylcyclohexyl)methanol

Disolventes

Condiciones de reacción

Temperatura
15°CELSIUS
Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

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

Procedimiento

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.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US07670504B2uspto-grants-2010_03