Sodium Hydroxide → 3-Benzylbenzyl alcohol

HRID 1451512Notes

Reaction equation

HRID 1451512 reaction equation
[CH2:1]([C:8]1[CH:9]=[C:10]([CH:14]=[CH:15][CH:16]=1)[C:11](O)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>C1COCC1.O.C(OCC)C>[CH2:1]([C:8]1[CH:9]=[C:10]([CH:14]=[CH:15][CH:16]=1)[CH2:11][OH:12])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 41245533-Benzylbenzoic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 5976133-Benzylbenzyl alcoholYield 85.7%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 3-benzylbenzoic acid (15 g, 70 mmol) in THF (100 ml) a solution of lithium aluminiumhydride in THF (80 ml, 80 mmol, 1M) was added dropwise. When addition was complete the mixture was stirred for 30 minutes at ambient temperature and then heated at reflux for 40 minutes. The reaction mixture was allowed to cool and water (3 ml), diethyl ether (100 ml), 4N sodium hydroxide (6 ml) and water (12 ml) were added successively. The mixture was stirred for 30 minutes, filtered and the solvent evaporated in vacuo. The residue was dissolved in toluene (200 ml) and dried (MgSO4) overnight. The solvent was evaporated in vacuo to give 11.9 g of crude 3-benzylbenzylalcohol as an oil.

Workup

  1. additionwas added dropwise
  2. additionWhen addition
  3. temperatureheated
  4. temperatureat reflux for 40 minutes
  5. temperatureto cool
  6. stirringThe mixture was stirred for 30 minutes
  7. filtrationfiltered
  8. customthe solvent evaporated in vacuo
  9. dissolutionThe residue was dissolved in toluene (200 ml)
  10. dry with materialdried (MgSO4) overnight
  11. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-3ca691b6bf7a413996d217b18452a521
Source dataset
uspto-grants-1997_02
Patent number
US05604242

Reaction notes

Loading…