Hydrochloric Acid → 3-(4-Methoxyphenyl)-1-propanol

HRID 704397Notes

Reaction equation

HRID 704397 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11](O)=[O:12])=[CH:5][CH:4]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.Cl>CCOCC>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH2:11][OH:12])=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 957503-(p-Methoxyphenyl)propionic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 794063-(4-Methoxyphenyl)-1-propanol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of the 3-(4-methoxyphenyl)propionic acid in 100 ml of anhydrous ether was added dropwise to a suspension of 1.10 g of lithium aluminum hydride in 50 ml of anhydrous ether with stirring at room temperature over 20 minutes. After stirring at room temperature for 30 minutes, the mixture was refluxed for 1 hours. After cooling, water was added with ice cooling, and the mixture was made acidic by further addition of 10% hydrochloric acid and then extracted with ether. The organic layer was washed with saturated aqueous solution of sodium chloride, driven over anhydrous magnesium sulfate and concentrated under reduced pressure to give 5.06 g of 3-(4-methoxyphenyl)propanol.

Workup

  1. stirringAfter stirring at room temperature for 30 minutes
  2. temperaturethe mixture was refluxed for 1 hours
  3. temperatureAfter cooling
  4. extractionextracted with ether
  5. washThe organic layer was washed with saturated aqueous solution of sodium chloride
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1d52cf5b199142f59c4a92e1f9919d49
Source dataset
uspto-grants-1991_01
Patent number
US04987132

Reaction notes

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