Potassium Carbonate → Methyl [4-(3-hydroxypropyl)phenoxy]acetate

HRID 882934Notes

Reaction equation

HRID 882934 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][OH:11])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:19][C:20]([O:22][CH3:23])=[O:21]>CC(C)=O>[CH3:23][O:22][C:20](=[O:21])[CH2:19][O:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][CH2:10][OH:11])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 824523-(4-Hydroxyphenyl)propanol

Product 1

HCID 22949949Methyl [4-(3-hydroxypropyl)phenoxy]acetate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 3-(4-hydroxyphenyl)-1-propanol (3 g, 19.7 mmol) in acetone (30 mL) is added potassium carbonate (4.08 g, 29.5 mmol) and methyl bromoacetate (2.8 mL, 29.3 mmol) and the reaction is heated at reflux for 15 h. The reaction mixture is allowed to cool to RT, filtered, and the solvent removed in vacuo. The residue is purified by chromatography (SiO2, EtOAc:iso-hexane, 2:3) to afford the title compound. 1H NMR (400 MHz, CDCl3) δ 7.14 (2H, d), 6.85 (2H, d), 4.64 (2H, s), 3.82 (3H, s), 3.69 (2H, t), 2.68 (2H, t), 1.82 (2H, m).

Workup

  1. temperaturethe reaction is heated
  2. temperatureat reflux for 15 h
  3. filtrationfiltered
  4. customthe solvent removed in vacuo
  5. customThe residue is purified by chromatography (SiO2, EtOAc:iso-hexane, 2:3)

Sources & evidence

ORD record
ord-b05beee6aa024ff6b6521cf0a20f0fd5
Source dataset
uspto-grants-2012_08
Patent number
US08236808B2

Reaction notes

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