Hydrochloric Acid → 3-Hydroxybenzenepropanol

HRID 1250115Notes

Reaction equation

HRID 1250115 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C[O:8][C:9](=O)[CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([OH:18])[CH:13]=1.O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+].Cl>O1CCCC1.O>[OH:8][CH2:9][CH2:10][CH2:11][C:12]1[CH:13]=[C:14]([OH:18])[CH:15]=[CH:16][CH:17]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 62649Sodium sulfate decahydrateHCID 1512675Methyl 3-(3-hydroxyphenyl)propionateHCID 21226445Aluminium lithium hydride

Product 1

HCID 103518713-HydroxybenzenepropanolYield 88%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

1.0M Lithium aluminum hydride in tetrahydrofuran (35.07 mL, 35.07 mmol) was added to a solution of 3-(3-hydroxyphenyl)propionic acid methyl ester (3.16 g, 17.5 mmol) in tetrahydrofuran (30 mL) at 0-5° C. under an argon atmosphere. The mixture was stirred at room temperature for 6 hours, and sodium sulfate decahydrate (15 g) was added to the mixture, followed by cooling to 0-5° C., and a dropwise addition of water (about 10 mL) and concentrated hydrochloric acid to pH 2-3. The mixture was extracted with ethyl acetate, and the extract was washed with water, brine, dried over magnesium sulfate, and concentrated to dryness. Purification by flash chromatography, eluting with hexane/ethyl acetate, gave 3-(3-hydroxypropyl)phenol as a clear oil (2.34 g, 88%).

Workup

  1. temperatureby cooling to 0-5° C.
  2. extractionThe mixture was extracted with ethyl acetate
  3. washthe extract was washed with water, brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated to dryness
  6. customPurification by flash chromatography
  7. washeluting with hexane/ethyl acetate

Sources & evidence

ORD record
ord-99f8da7ece674de9b449c38dab0e4a2b
Source dataset
uspto-grants-2002_01
Patent number
US06335459B1

Reaction notes

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