Water → 4-Ethyl-3-(3-hydroxy-propoxy)-benzoic acid methyl ester

HRID 1158444Notes

Reaction equation

HRID 1158444 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH3:11])=[C:6]([OH:12])[CH:5]=1.Br[CH2:15][CH2:16][CH2:17][OH:18].C([O-])([O-])=O.[K+].[K+].O>C(#N)C>[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH3:11])=[C:6]([O:12][CH2:15][CH2:16][CH2:17][OH:18])[CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 123083-Bromo-1-propanolHCID 54428408Methyl 4-ethyl-3-hydroxybenzoate

Product 1

HCID 686170744-Ethyl-3-(3-hydroxy-propoxy)-benzoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 4-ethyl-3-hydroxy-benzoic acid methyl ester (3.21 g, 17.81 mmol) in acetonitrile (35 mL) are added 3-bromo-1-propanol (1.85 mL, 21.37 mmol) and K2CO3 (3.69 g, 26.7 mmol). The solution is refluxed for 4 h, then poured into water and extracted three times with AcOEt. The combined organic extracts are washed with brine, dried over Na2SO4, filtered and concentrated to give the title product. TLC, Rf (c-hexane/AcOEt 8:2)=0.15, MS (LC-MS): 239.2 [M+H]+, tR (HPLC, Macherey-Nagel Nucleosil C18 column, 10-100% CH3CN/H2O/5 min, 100% CH3CN/3 min, flow: 1.5 ml/min): 5.10 min.

Workup

  1. temperatureThe solution is refluxed for 4 h
  2. extractionextracted three times with AcOEt
  3. washThe combined organic extracts are washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-567c4c1ab79b47d4a2ecbde0da67d8e2
Source dataset
uspto-grants-2010_10
Patent number
US07807709B2

Reaction notes

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