Methyl iodide → HCID 20119783, compound

HRID 1516411Notes

Reaction equation

HRID 1516411 reaction equation
[OH:1][CH2:2][CH2:3][S:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][CH:6]=1.[H-].[Na+].[CH3:16]I>CN(C=O)C>[CH3:16][O:1][CH2:2][CH2:3][S:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 607758HCID 607758, compound

Product 1

HCID 20119783HCID 20119783, compoundYield 60.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
27.5 °C

Procedure

To a stirred solution of 4-(2-Hydroxy-ethylsulfanyl)-benzoic acid (7 g, 0.0352 mol) in DMF (140 mL) was added Sodium hydride (4.2 g, 0.088 mmol) at 5-10° C. under nitrogen atmosphere. Reaction mixture was stirred for 15 min at 25-30° C. and then Methyl iodide (6.6 mL, 0.1057mol) was added to at 10-15° C. Stirring continued for 3 hr after removing cooling. Reaction mixture was then quenched in aqueous NaOH solution and stirred for 30 min. Aqueous layer was washed with ethyl acetate (200 mL). Aqueous layer was then acidified using dil.HCl. Product obtained was filtered which on drying afforded 4.5 g of desired product in 60% yield.

Workup

  1. customReaction mixture
  2. stirringStirring
  3. waitcontinued for 3 hr
  4. customafter removing
  5. temperaturecooling
  6. customReaction mixture
  7. customwas then quenched in aqueous NaOH solution
  8. stirringstirred for 30 min
  9. washAqueous layer was washed with ethyl acetate (200 mL)
  10. customProduct obtained
  11. filtrationwas filtered which
  12. customon drying

Sources & evidence

ORD record
ord-9475a8fadbbd4933bc5f0d800ea04667
Source dataset
uspto-grants-2012_07
Patent number
US08227492B2

Reaction notes

Loading…