Methyl iodide → 3-(4-Methoxyphenyl)-1-propanol

HRID 2415427Notes

Reaction equation

HRID 2415427 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][OH:11])=[CH:4][CH:3]=1.[C:12](=O)([O-])[O-].[K+].[K+].CI>CC(C)=O.O>[CH3:12][O:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][CH2:10][OH:11])=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 824523-(4-Hydroxyphenyl)propanol

Product 1

HCID 794063-(4-Methoxyphenyl)-1-propanolYield 95.1%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Conditions

Temperature
65 °C

Procedure

2.26 g (14.87 mmoles) of 3-(4-hydroxyphenyl)-1-propanol were dissolved in dry acetone (20 ml) and potassium carbonate (2.05 g, 14.87 mmoles) was added, followed by methyl iodide (MeI) (2.11 g, 14.87 mmoles). The mixture was kept at reflux in a water bath at 60-70° C. for 48 h. After that period of time, it was diluted with water and the acetone was removed at reduced pressure. Extraction was performed with diethyl ether, and the result was washed with water, dried over sodium sulphate, filtered and the solvent was evaporated in a vacuum to give an oil (2.35 g) (94.93% yield) of 3-(4-methoxyphenyl)-1-propanol.

Workup

  1. customthe acetone was removed at reduced pressure
  2. extractionExtraction
  3. washthe result was washed with water
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. customthe solvent was evaporated in a vacuum

Sources & evidence

ORD record
ord-fada1259576841dc90fcba18b20a5d24
Source dataset
uspto-grants-2004_11
Patent number
US06818780B2

Reaction notes

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