4-Hydroxybenzoic Acid → 4-(2-Propyloxyethoxy)benzoic Acid

HRID 11404

Reaction equation

HRID 11404 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:17]([O:20][CH2:21][CH2:22]Cl)[CH2:18][CH3:19].O>CN(C)C=O>[CH2:17]([O:20][CH2:21][CH2:22][O:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1)[CH2:18][CH3:19]

Participants

6

Reactant 4

HCID 1354-Hydroxybenzoic AcidHCID 962WaterHCID 11430Potassium CarbonateHCID 1235061-(2-Chloroethoxy)propane

Product 1

HCID 219742854-(2-Propyloxyethoxy)benzoic AcidYield 105.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-hydroxybenzoic acid (3.04 g) and anhydrous potassium carbonate (5.52 g) in N,N-dimethylformamide (20 ml) was added 2-propyloxyethyl chloride (2.94 g), and the mixture was stirred at room temperature overnight, and then stirred at 80° C. for 8 hours. To a reaction solution was added water, and then the mixture was extracted with ethyl acetate. The organic layer was washed with water and a saturated aqueous solution of sodium chloride, successively, dried and concentrated under reduced pressure to give the title compound (5.21 g; crude).

Workup

  1. stirringstirred at 80° C. for 8 hours
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materiala saturated aqueous solution of sodium chloride, successively, dried
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4cc1be09091443928f00b584eef1d8bf
Source dataset
uspto-grants-2006_08
Patent number
US07098234B2

Linked notes

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