Aluminium lithium hydride → Phenol, 3-(2-hydroxyethoxy)-

HRID 1352877Notes

Reaction equation

HRID 1352877 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:10][C:11]1[CH:12]=[C:13]([CH:21]=[CH:22][CH:23]=1)[O:14][CH2:15][C:16](OCC)=[O:17])(=O)C>O1CCCC1>[OH:17][CH2:16][CH2:15][O:14][C:13]1[CH:12]=[C:11]([OH:10])[CH:23]=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 86594026HCID 86594026, compound

Product 1

HCID 152273Phenol, 3-(2-hydroxyethoxy)-

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of lithium aluminum hydride (455 mg, 12 mmol) in tetrahydrofuren was dropped ethyl [3-(acetyloxy)phenoxy]acetate (1.19 g, 5 mmol) in tetrahydrofuran (20 ml) at room temperature, and the mixture was stirred for 2 hours at room temperature. The reaction was quenched by 10% hydrochloric acid and the mixture was extracted with ethyl acetate. The organic layer was washed with water, 10% hydrochloric acid, an aqueous saturated sodium hydrogencarbonate solution and an aqueous saturated sodium chloride solution. The organic layer was dried over sodium sulfate. The solvent was removed under reduced pressure to give 3-(2-hydroxyethoxy)phenol (864 mg, quantitatively).

Workup

  1. customThe reaction was quenched by 10% hydrochloric acid
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water, 10% hydrochloric acid
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-ef28776f56a04eea9ba4e8638b4846c9
Source dataset
uspto-grants-2007_05
Patent number
US07220773B2

Reaction notes

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