Hydrochloric Acid → 2-(4-Methoxyphenyl)propan-1-ol

HRID 26674Notes

Reaction equation

HRID 26674 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([CH3:14])[C:10](OC)=[O:11])=[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]([CH:9]([CH3:14])[CH2:10][OH:11])=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 12398855Methyl 2-(4-methoxyphenyl)propanoateHCID 21226445Aluminium lithium hydride2×

Product 1

HCID 3164752-(4-Methoxyphenyl)propan-1-olYield 89.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Methyl 2-(4-methoxyphenyl)propionate (11.39 g; 0.0586 mol) was dissolved in dry ether (25 ml) and slowly added to a stirred suspension of lithium aluminium hydride (4.59 g; 0.121 mol;) in dry ether (60 ml); the temperature was maintained below 25° C. by cooling. Stirring at ambient temperature was continued for 1 hour. Water was cautiously added dropwise to decompose the unreacted lithium aluminium hydride and the inorganic salts were dissolved by the addition of dilute hydrochloric acid. The ether was separated and the aqueous phase re-extracted with ether (2×100 ml). The combined ether extracts were washed with water, saturated sodium bicarbonate solution, water, and then dried over magnesium sulphate. The product was isolated as a pale yellow oil (8.72 g) following evaporation of the solvent.

Workup

  1. temperaturethe temperature was maintained below 25° C.
  2. temperatureby cooling
  3. customThe ether was separated
  4. extractionthe aqueous phase re-extracted with ether (2×100 ml)
  5. washThe combined ether extracts were washed with water, saturated sodium bicarbonate solution, water
  6. dry with materialdried over magnesium sulphate

Sources & evidence

ORD record
ord-1e1f3f1f1b1f4c199d6ef41fa0de472d
Source dataset
uspto-grants-1979_04
Patent number
US04151179

Reaction notes

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