Aluminium lithium hydride → 4-Methyl-3-phenyl-4-penten-1-ol

HRID 2387594Notes

Reaction equation

HRID 2387594 reaction equation
[CH3:1][C:2](=[CH2:15])[CH:3]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH2:4][C:5](OC)=[O:6].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH3:15][C:2](=[CH2:1])[CH:3]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH2:4][CH2:5][OH:6]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 58435475Methyl 4-methyl-3-phenyl-4-pentenoate

Product 1

HCID 146915204-Methyl-3-phenyl-4-penten-1-olYield 97.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

The methyl 4-methyl-3-phenyl-4-pentenoate (258.3 g, 1.251 mol) was added, at 0° C. under nitrogen, to lithium aluminum hydride (25 g, 0.625 mol) in dry THF (1 liter), drop-wise. After 30 minutes, the cooling bath was removed and the reaction allowed reaching room temperature. After 24 h, more THF (1 liter) was added and the reaction was cooled to 0° C. and treated successively with water (25 ml), 5% aqueous sodium hydroxide (75 ml) and water (25 ml). The reaction was stirred at room temperature for 30 minutes. Anhydrous solid sodium sulfate was added (100 g) and stirring continued for 5 minutes The solid was filtered off, rinsed with diethyl ether and the filtrate was evaporated under vacuum. The product was purified distillation through a 20-cm Widmer column. 214 g of the desired product were obtained (yield=97%).

Workup

  1. customthe cooling bath was removed
  2. customallowed reaching room temperature
  3. waitAfter 24 h
  4. additionmore THF (1 liter) was added
  5. additiontreated successively with water (25 ml), 5% aqueous sodium hydroxide (75 ml) and water (25 ml)
  6. additionAnhydrous solid sodium sulfate was added (100 g)
  7. stirringstirring
  8. waitcontinued for 5 minutes
  9. filtrationThe solid was filtered off
  10. washrinsed with diethyl ether
  11. customthe filtrate was evaporated under vacuum
  12. customThe product was purified
  13. distillationdistillation through a 20-cm Widmer column

Sources & evidence

ORD record
ord-757f663236a54bc2be0f9c0ebea667ba
Source dataset
uspto-grants-2012_09
Patent number
US08268895B2

Reaction notes

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