Dimethylformamide → Methyl 4-(MethoxyMethyl)benzoate

HRID 1883201Notes

Reaction equation

HRID 1883201 reaction equation
[OH:1][CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7](O)=[O:8])=[CH:5][CH:4]=1.[H-].[Na+].I[CH3:15].CN([CH:19]=[O:20])C>>[CH3:15][O:1][CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([O:20][CH3:19])=[O:8])=[CH:5][CH:4]=1

Participants

5

Reactant 4

HCID 6228Dimethylformamide2×HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 763604-(Hydroxymethyl)benzoic acid

Product 1

HCID 15247548Methyl 4-(MethoxyMethyl)benzoateYield 72%

Conditions

Temperature
0 °C

Procedure

Under nitrogen atmosphere, a solution of 4-(hydroxymethyl)-benzoic acid (5.00 g) in DMF (200 mL) was cooled to 0° C., and thereto was added NaH (2.76 g, 60%). The mixture was stirred at the same temperature for 10 minutes, and stirred at room temperature for 20 minutes. The mixture was cooled to 0° C., and thereto were added DMF (100 mL) and iodomethane (18.7 g), and the mixuture was stirred at room temperature for 48 hours. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column (hexane/ethyl acetate=15/1) to give methyl 4-(methoxymethyl)benzoate (4.27 g, 72%).

Workup

  1. stirringstirred at room temperature for 20 minutes
  2. stirringthe mixuture was stirred at room temperature for 48 hours
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue was purified by silica gel column (hexane/ethyl acetate=15/1)

Sources & evidence

ORD record
ord-f4333b2d8934450683ea1e59a50ec8a4
Source dataset
uspto-grants-2004_07
Patent number
US06759429B2

Reaction notes

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