Isopropyl iodide → 2,4-Bis(ethoxymethoxy)-1-isopropoxybenzene

HRID 1511214Notes

Reaction equation

HRID 1511214 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7]([O:9][CH2:10][O:11][C:12]1[CH:17]=[C:16]([O:18][CH2:19][O:20][CH2:21][CH3:22])[CH:15]=[CH:14][C:13]=1[OH:23])[CH3:8].I[CH:25]([CH3:27])[CH3:26]>CN(C)C=O>[CH2:7]([O:9][CH2:10][O:11][C:12]1[CH:17]=[C:16]([O:18][CH2:19][O:20][CH2:21][CH3:22])[CH:15]=[CH:14][C:13]=1[O:23][CH:25]([CH3:27])[CH3:26])[CH3:8]

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 251402532,4-Bis(ethoxymethoxy)phenol

Product 1

HCID 251409942,4-Bis(ethoxymethoxy)-1-isopropoxybenzeneYield 55%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium carbonate (2.85 g, 20.7 mmol) was added to 3a (500 mg, 2.07 mmol) in N,N-dimethylformamide (4.10 mL) at room temperature. After 10 minutes, 2-iodopropane (2.06 mL, 20.7 mmol) was added and the solution was heated to reflux for 12 hours. Upon cooling to room temperature, the solution was extracted with EtOAc (3×20 mL); combined organic fractions were washed with saturated aqueous NaCl, dried (Na2SO4), filtered, and concentrated. The residue was purified via column chromatography (SiO2, 5:1→1:1 Hexane:EtOAc) to afford 4c as a yellow oil (0.32 g, 55%): 1H NMR (CD2Cl2, 400 MHz) δ 6.87 (s, 1H), 6.86 (d, J=4.9 Hz, 1H), 6.66 (dd, J=11.6, 3.4 Hz, 1H), 5.23 (s, 2H), 5.17 (s, 2H), 4.44-4.38 (m, 1H), 3.83-3.72 (m, 4H), 1.33 (s, 3H), 1.31 (s, 3H), 1.27-1.23 (m, 6H); 13C NMR (CDCl3, 125 MHz) δ 152.4, 149.1, 143.2, 118.6, 109.5, 107.5, 94.4, 93.9, 72.8, 64.3, 64.1, 22.2 (2C), 15.1, 15.1; IR (film) νmax 2976, 1591, 1504, 1528, 1391, 1258, 1217, 1107, 1011, 847 cm−1; HRMS (ESI+) m/z: [M+H]+ calcd for C15H24O5, 285.1702. found, 285.1746; [M+Na]+ calcd for C15H24O5, 307.1522. found, 307.1310.

Workup

  1. temperaturethe solution was heated
  2. temperatureto reflux for 12 hours
  3. extractionthe solution was extracted with EtOAc (3×20 mL)
  4. washcombined organic fractions were washed with saturated aqueous NaCl
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified via column chromatography (SiO2, 5:1→1:1 Hexane:EtOAc)

Sources & evidence

ORD record
ord-18915ebeaf644f1f89f3d2af2d9ab627
Source dataset
uspto-grants-2012_07
Patent number
US08212011B2

Reaction notes

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