Ethylparaben → HCID 59504711, compound

HRID 2400546Notes

Reaction equation

HRID 2400546 reaction equation
[OH:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:20][CH2:21][O:22][CH2:23][CH2:24][O:25][CH3:26]>COCCOC.[I-].[K+]>[CH3:26][O:25][CH2:24][CH2:23][O:22][CH2:21][CH2:20][O:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:11][CH:12]=1

Participants

6

Reactant 3

HCID 8434EthylparabenHCID 11430Potassium CarbonateHCID 1235321-Bromo-3,6-dioxaheptane

Product 1

HCID 59504711HCID 59504711, compoundYield 67.2%

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of ethyl 4-hydroxybenzoate (2.0 g, 12.04 mmol) in dry DME (50 mL) was added potassium carbonate (3.33 g, 24.07 mmol), potassium iodide (100 mg, 0.602 mmol) and 1-bromo-2-(2-methoxyethoxy)ethane (3.6 mL, 24.07 mmol). The mixture was stirred at reflux for 2 days. After being cooled to rt, the solids were removed by filtration and the solvent by evaporation in vacuo. The remaining crude product was purified by MPLC (silica, cyclohexane/ethyl acetate 5:1) to afford the title compound (2.17 g, 67%): 1H NMR (400 MHz, CDCl3) δ 7.98 (d, 2H), 6.93 (d, 2H), 4.33 (quart, 2H), 4.19 (t, 2H), 3.88 (t, 2H), 3.72 (t, 2H), 3.57 (t, 2H), 3.39 (s, 3H), 1.37 (t, 3H); DCI(NH3)-MS m/z 286 (M+NH4)+; HPLC RT (Method I) 4.14 min.

Workup

  1. temperatureat reflux for 2 days
  2. customthe solids were removed by filtration
  3. customthe solvent by evaporation in vacuo
  4. customThe remaining crude product was purified by MPLC (silica, cyclohexane/ethyl acetate 5:1)

Sources & evidence

ORD record
ord-6bd41f186f24451eaf764ffa59603679
Source dataset
uspto-grants-2014_08
Patent number
US08796253B2

Reaction notes

Loading…