Water → Ethyl 3-isopropoxybenzoate

HRID 1610642Notes

Reaction equation

HRID 1610642 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6].[CH:13](Br)([CH3:15])[CH3:14].[I-].[Na+].O>CN(C)C=O>[CH:13]([O:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6])([CH3:15])[CH3:14]

Participants

6

Reactant 4

HCID 962WaterHCID 5238Sodium IodideHCID 63582-BromopropaneHCID 24522Ethyl 3-hydroxybenzoate

Product 1

HCID 22261418Ethyl 3-isopropoxybenzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of ethyl 3-hydroxybenzoate (15.2 g, 0.10 mol) in N,N-dimethylformamide (100 ml) were added isopropyl bromide (12.1 ml, 0.13 mol) and sodium iodide (19.5 g, 0.13 mol), and the mixture was stirred at 70° C. for 15 hrs. To the reaction solution was added water (500 ml), and the mixture was extracted with ethyl acetate (500,200 ml). The extract was washed with water, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was purified by silica gel chromatography (hexane:ethyl acetate=10:1) to give the objective substance (12.4 g, 64%) as an oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate (500,200 ml)
  2. washThe extract was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated under reduced pressure
  5. customThe residue was purified by silica gel chromatography (hexane:ethyl acetate=10:1)
  6. customto give the objective substance (12.4 g, 64%) as an oil

Sources & evidence

ORD record
ord-508b332b6036428d89cb4bf82f7d77ee
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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