Iodoethane → Methyl 4-ethoxy-2-hydroxybenzoate

HRID 1445457Notes

Reaction equation

HRID 1445457 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([OH:12])[C:5](=[CH:10][CH:11]=1)[C:6]([O:8][CH3:9])=[O:7].[CH2:13](I)[CH3:14].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:13]([O:1][C:2]1[CH:3]=[C:4]([OH:12])[C:5](=[CH:10][CH:11]=1)[C:6]([O:8][CH3:9])=[O:7])[CH3:14]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 16523Methyl 2,4-Dihydroxybenzoate

Product 1

HCID 4389058Methyl 4-ethoxy-2-hydroxybenzoateYield 54.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl 4-hydroxysalicylate (10.0 g, 59.5 mmol) was dissolved in DMF. Ethyl iodide (9.74 g, 62.4 mmol) was added, followed by potassium carbonate (8.63 g, 62.4 mmol), and the reaction mixture was stirred under N2 at room temperature for 18 h. The reaction mixture was concentrated in vacuo to remove the majority of the DMF, and the residue taken up in EtOAc, and washed with water (2×), dried, and concentrated in vacuo to give an off-white solid. Recrystallization from hexane gave 6.41 g, (54.9%) of methyl 4-ethoxysalicylate as an off-white solid.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customto remove the majority of the DMF
  3. washwashed with water (2×)
  4. customdried
  5. concentrationconcentrated in vacuo
  6. customto give an off-white solid
  7. customRecrystallization from hexane

Sources & evidence

ORD record
ord-f9a76b25cbf64b2982901a266ff0bd40
Source dataset
uspto-grants-2010_02
Patent number
US07666866B2

Reaction notes

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