Water → 2-[2-(Hydroxymethyl)phenyl]ethanol

HRID 2706

Reaction equation

HRID 2706 reaction equation
[C:1](O)(=[O:12])[CH2:2][C:3]1[C:4](=[CH:8][CH:9]=[CH:10][CH:11]=1)[C:5](O)=[O:6].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[OH:6][CH2:5][C:4]1[CH:8]=[CH:9][CH:10]=[CH:11][C:3]=1[CH2:2][CH2:1][OH:12]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 66643Homophthalic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 2390242-[2-(Hydroxymethyl)phenyl]ethanolYield 98,293.703%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Dissolve homophthalic acid (22.2 g, 0.123 mmol) in tetrahydrofuran (250 mL) and add dropwise at room temperature to a slurry of lithium aluminum hydride (15.5 g, 0.407 mol) in tetrahydrofuran (500 mL). Heat at reflux for 18 hours, cool in an ice bath and carefully add, by dropwise addition, water (16 mL), followed by 50% sodium hydroxide (16 mL). Remove the ice bath, add water slowly with stirring and stir until the gray precipitate turns white and evolution of gas ceases. Filter, wash solids with methylene chloride, dry (MgSO4) and evaporate the solvent in vacuo to give 2-(2-hydroxymethyl-phenyl)-ethanol as a viscous oil (18.4 g, 98%).

Workup

  1. temperatureHeat
  2. temperatureat reflux for 18 hours
  3. temperaturecool in an ice bath
  4. customRemove the ice bath
  5. additionadd water slowly
  6. stirringstir until the gray precipitate
  7. filtrationFilter
  8. washwash solids with methylene chloride
  9. dry with materialdry (MgSO4)
  10. customevaporate the solvent in vacuo

Sources & evidence

ORD record
ord-eb64b8ce0a9f4ad097d9d9c05791fc8a
Source dataset
uspto-grants-1998_03
Patent number
US05731306

Linked notes

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