Methyl iodide → 4-(4-Hydroxyphenyl)butanoic acid methyl ester

HRID 2417257Notes

Reaction equation

HRID 2417257 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][C:11]([OH:13])=[O:12])=[CH:4][CH:3]=1.[C:14](=O)(O)[O-].[Na+].IC>CN(C=O)C.O>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 2799834-(4-Hydroxyphenyl)butanoic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 1409044-(4-Hydroxyphenyl)butanoic acid methyl esterYield 74.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 0.69 g of 4-(4-hydroxyphenyl)butyric acid in 10 mL of DMF was added 0.956 g of sodium bicarbonate followed by 0.36 mL of iodomethane and the resulting mixture was stirred at room temperature for 5 h. The reaction was then diluted with water, extracted with ether, dried over MgSO4, filtered and concentrated in vacuo to provide 0.553 g of methyl 4-(4-hydroxyphenyl)butyrate.

Workup

  1. extractionextracted with ether
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3e49e9b19d274564997fc78c54c79f5d
Source dataset
uspto-grants-2004_11
Patent number
US06825354B2

Reaction notes

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