Benzeneacetic acid, 4-hydroxy-, methyl ester → Tyrosol

HRID 2249581Notes

Reaction equation

HRID 2249581 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9](OC)=[O:10])=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][OH:10])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 518900Benzeneacetic acid, 4-hydroxy-, methyl esterHCID 21226445Aluminium lithium hydride

Product 1

HCID 10393TyrosolYield 44.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of methyl 2-(4-hydroxyphenyl)acetate (3.0 g, 18.07 mmol), in THF (20 mL) was added to a stirred suspension of LAH (0.89 g, 23.49 mmol) in THF (20 mL) at 0° C. The stirring was continued at RT for 4 h. Excess of LAH was quenched with saturated Na2SO4 solution and the precipitate formed was filtered off. The filtrated was extracted with ethyl acetate and the organic extract was washed with brine, dried (Na2SO4) and evaporated to dryness. Column purification with 50% ethyl acetate-pet ether yielded the title compound (1.1 g, 44%) as a white solid.

Workup

  1. customExcess of LAH was quenched with saturated Na2SO4 solution
  2. customthe precipitate formed
  3. filtrationwas filtered off
  4. extractionThe filtrated was extracted with ethyl acetate
  5. extractionthe organic extract
  6. washwas washed with brine
  7. dry with materialdried (Na2SO4)
  8. customevaporated to dryness
  9. customColumn purification with 50% ethyl acetate-pet ether

Sources & evidence

ORD record
ord-7fdfa504f88f4fde97e2788cbe10b791
Source dataset
uspto-grants-2008_01
Patent number
US07314889B2

Reaction notes

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