Hydrochloric Acid → 3-(4-Hydroxyphenyl)propanol

HRID 1242260Notes

Reaction equation

HRID 1242260 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](O)=[O:17])=[CH:10][CH:9]=1.Cl>C1COCC1.O>[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

6

Reactant 3

HCID 313Hydrochloric AcidHCID 103943-(4-Hydroxyphenyl)propionic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 824523-(4-Hydroxyphenyl)propanolYield 69.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
60 °C

Procedure

To a suspension of LiAlH4 (8.37 g, 220.6 mmol, 1.5 equiv) in THF (300 ml) was added dropwise a solution of 3-(4-hydroxyphenyl)propionic acid (25.0 g, 150 mmol, 1 equiv) in THF (50 ml) at rt and mixture stirred at 60° C. for 2 h. The reaction mixture was acidified with 1 N HCl, diluted with water, and extracted with EtOAc. The combined extracts were washed with water, saturated aqueous NaHCO3, brine and dried over MgSO4 and concentrated under vacuum to give a 3-(4-hydroxyphenyl)-1-propanol as a white solid (15.95 g, 69.9%).

Workup

  1. extractionextracted with EtOAc
  2. washThe combined extracts were washed with water, saturated aqueous NaHCO3, brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-72e99c8533a740cb8f7208583a413628
Source dataset
uspto-grants-2006_10
Patent number
US07115666B2

Reaction notes

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