Benzenepropanoic acid, 4-hydroxy-, methyl ester → 3-(4-Hydroxyphenyl)propanol

HRID 1817689Notes

Reaction equation

HRID 1817689 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][C:16](OC)=[O:17])=[CH:10][CH:9]=1>C1COCC1>[OH:7][C:8]1[CH:9]=[CH:10][C:11]([CH2:14][CH2:15][CH2:16][OH:17])=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 79706Benzenepropanoic acid, 4-hydroxy-, methyl esterHCID 21226445Aluminium lithium hydride

Product 1

HCID 824523-(4-Hydroxyphenyl)propanolYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of LAH (22.1 g, 2.5 eq, 583 mmol) in dry THF (1.0 L), was added dropwise a THF (50 mL) solution of methyl 3-(4-hydroxyphenyl)propionate (21 g, 10 eq, 116 mmol) at RT. The reaction mixture was refluxed for 4-5 h. It was worked up by quenching with excess ethyl acetate followed by addition of water (23 mL), 15% aq. NaOH (23 mL) and water (70 mL) under controlled stirring and maintaining RT. To the workup mixture conc. HCl was added to adjust the pH at 7.0. It was then filtered through celite and washed with ethyl acetate. Combined filtrate was dried (Na2SO4) and condensed. Obtained residue was chromatographed (ethyl acetate/hexanes) to obtain 3-(4-hydroxyphenyl)propanol (17 g, 100%) as white solid. Mp: 52-54° C.

Workup

  1. temperatureThe reaction mixture was refluxed for 4-5 h
  2. customby quenching with excess ethyl acetate
  3. additionfollowed by addition of water (23 mL), 15% aq. NaOH (23 mL) and water (70 mL)
  4. additionTo the workup mixture conc. HCl was added
  5. filtrationIt was then filtered through celite
  6. washwashed with ethyl acetate
  7. customCombined filtrate was dried
  8. custom(Na2SO4) and condensed
  9. customObtained residue was chromatographed (ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-8e6ad976d4804823bc181ad1b639b964
Source dataset
uspto-grants-2009_10
Patent number
US07598293B2

Reaction notes

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