Tetrahydrofuran → 3-(4-Hydroxyphenyl)propanol

HRID 2415426Notes

Reaction equation

HRID 2415426 reaction equation
C([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][C:12]([OH:14])=O)=[CH:6][CH:5]=1)(=O)C.[O:15]1CCCC1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O>[OH:15][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][CH2:12][OH:14])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 3128833-(4-acetylphenyl) propionic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 824523-(4-Hydroxyphenyl)propanolYield 65%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 3.82 g (17.36 mmoles) of methyl ester of 3-(4-acetylphenyl) propionic acid were added 100 ml of dry tetrahydrofurane. To this solution were slowly added 1.80 g (47.43 mmoles) of lithium aluminium hydride (LiAlH4). The reaction mixture was refluxed in an argon atmosphere for 4 hours. At the end of the reaction, water was carefully added, extraction was performed three times with diethyl ether and the result was vacuum dried over anhydrous sodium sulphate, giving 1.70 g (65% yield) of 3-(4-hydroxyphenyl)-1-propanol. Crystallisation in methanol gave a white crystalline solid m,.p.=52-53° C.

Workup

  1. temperatureThe reaction mixture was refluxed in an argon atmosphere for 4 hours
  2. additionwas carefully added
  3. extractionextraction
  4. dry with materialdried over anhydrous sodium sulphate

Sources & evidence

ORD record
ord-394c5c7dc81d4cbbb7584b9649f69286
Source dataset
uspto-grants-2004_11
Patent number
US06818780B2

Reaction notes

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