Aluminium lithium hydride → 3-(4-Hydroxymethyl-2,6-dimethyl-phenyl)-propan-1-ol

HRID 2240771Notes

Reaction equation

HRID 2240771 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH:7][CH2:8][C:9]1[CH:14]=[C:13]([CH3:15])[C:12]([CH2:16][CH2:17][C:18](O)=[O:19])=[C:11]([CH3:21])[CH:10]=1>C1COCC1>[OH:7][CH2:8][C:9]1[CH:14]=[C:13]([CH3:15])[C:12]([CH2:16][CH2:17][CH2:18][OH:19])=[C:11]([CH3:21])[CH:10]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydride2×HCID 574374033-(4-Hydroxymethyl-2,6-dimethyl-phenyl)-propionic acid

Product 1

HCID 574374073-(4-Hydroxymethyl-2,6-dimethyl-phenyl)-propan-1-olYield 98.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a suspension of LiAlH4 (219 mg, 5.76 mmol) in THF (35 mL), a solution of 3-(4-hydroxymethyl-2,6-dimethyl-phenyl)-propionic acid (1.0 g, 4.80 mmol, intermediate from Aldehyde 4) in THF (10 mL) is added dropwise. Upon complete addition the suspension is refluxed for 2 h. The suspension is diluted with THF (10 mL) and another portion of LiAlH4 (182 mg, 4.80 mmol) is added. The mixture is refluxed for further two hours, then cooled with an ice-bath. The reaction is carefully quenched by adding sat. aq. NH4Cl solution (2 mL) followed by 2 N aq. HCl until a clear solution forms. The mixture is diluted with water and extracted twice with EA. The combined organic extracts are dried over MgSO4, filtered and the solvent of the filtrate is evaporated to leave 3-(4-hydroxymethyl-2,6-dimethyl-phenyl)-propan-1-ol (920 mg) as a colourless crystalline solid; LC-MS: tR=0.70 min, [M+1−H2O]+=177.20.

Workup

  1. additionUpon complete addition the suspension
  2. temperatureis refluxed for 2 h
  3. temperatureThe mixture is refluxed for further two hours
  4. temperaturecooled with an ice-bath
  5. customThe reaction is carefully quenched
  6. additionby adding sat. aq. NH4Cl solution (2 mL)
  7. additionThe mixture is diluted with water
  8. extractionextracted twice with EA
  9. dry with materialThe combined organic extracts are dried over MgSO4
  10. filtrationfiltered
  11. customthe solvent of the filtrate is evaporated

Sources & evidence

ORD record
ord-6057f3109a474f75913e1c34999e290a
Source dataset
uspto-grants-2010_05
Patent number
US07723378B2

Reaction notes

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