Methyl iodide → Methyl 2-(4-hydroxymethylphenoxy)acetate

HRID 865443Notes

Reaction equation

HRID 865443 reaction equation
[OH:1][CH2:2][C:3]1[CH:13]=[CH:12][C:6]([O:7][CH2:8][C:9]([OH:11])=[O:10])=[CH:5][CH:4]=1.[CH:14](N(CC)C(C)C)(C)C.CI>CN(C=O)C>[OH:1][CH2:2][C:3]1[CH:13]=[CH:12][C:6]([O:7][CH2:8][C:9]([O:11][CH3:14])=[O:10])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 81531DiisopropylethylamineHCID 1942914-Hydroxymethylphenoxyacetic acid

Product 1

HCID 690034Methyl 2-(4-hydroxymethylphenoxy)acetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

18.2 g of 4-hydroxymethylphenoxyacetic acid are dissolved together with 17.1 ml of N,N-diisopropylethylamine in 50 ml of DMF, and then 6.1 ml of methyl iodide are added to the stirred solution. The mixture warms slightly during this. The reaction is complete after 3 h. The solvent is removed in vacuo. The residue is taken up in ether, and the solution is extracted once with 0.5 N hydrochloric acid. The aqueous phase is then extracted three times with ether, and the combined ether phases are washed with aqueous sodium bicarbonate solution and concentrated. The residue is dissolved in ethyl acetate and filtered through a short silica gel column. The pale yellowish oil which is obtained after concentration crystallizes on being left to stand.

Workup

  1. customThe solvent is removed in vacuo
  2. extractionthe solution is extracted once with 0.5 N hydrochloric acid
  3. extractionThe aqueous phase is then extracted three times with ether
  4. washthe combined ether phases are washed with aqueous sodium bicarbonate solution
  5. concentrationconcentrated
  6. dissolutionThe residue is dissolved in ethyl acetate
  7. filtrationfiltered through a short silica gel column
  8. customThe pale yellowish oil which is obtained
  9. concentrationafter concentration
  10. customcrystallizes
  11. waiton being left

Sources & evidence

ORD record
ord-a901564924a645e4851c43eb7f42c12d
Source dataset
uspto-grants-1996_10
Patent number
US05565606

Reaction notes

Loading…