Water → 2-(3,4-Dimethoxyphenoxy)ethanol

HRID 1272040Notes

Reaction equation

HRID 1272040 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([OH:11])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[H-].[Na+].[O:14]1C=CC=[CH:16][CH:15]1OCCBr.O>CC(N(C)C)=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:6]=[CH:7][C:8]=1[O:9][CH3:10])[O:11][CH2:16][CH2:15][OH:14]

Participants

6

Reactant 4

HCID 962WaterHCID 162513,4-DimethoxyphenolHCID 24758Sodium hydrideHCID 184563812-(2-Bromoethoxy)-2H-pyran

Product 1

HCID 122988832-(3,4-Dimethoxyphenoxy)ethanol

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A mixture of 3,4-dimethoxyphenol (155 mg, 1.0 mmol) and 60% sodium hydride (50 mg, 1.25 mmol) in DMA (6 ml) was stirred for 20 min under an atmosphere of nitrogen. 2-(2-Pyranyloxy)ethylbromide (220 mg, 1.0 mmol) was added dropwise. The reaction mixture was stirred for 6 hours at room temperature and then the mixture was poured into water (100 ml). The mixture was extracted with ethyl acetate (2×30 ml) and the combined organic extracts were dried (MgSO4). The organic phase was concentrated and the residue was dissolved in 2-propanol (30 ml) and 4 N HCl (20 ml) was added. The mixture was heated at reflux temperature for 30 min and then stirred at room temperature for 2 hours. The reaction mixture was concentrated and the residue was dissolved in ethyl acetate (50 ml). The organic solution was dried (MgSO4) and the solvent was evaporated. The oily residue was purified on silica gel (50 g) eluting with a mixture of heptane and ethyl acetate (3:2). This afforded 100 mg (50%) of 2-(3,4-dimethoxyphenoxy)ethanol.

Workup

  1. stirringThe reaction mixture was stirred for 6 hours at room temperature
  2. extractionThe mixture was extracted with ethyl acetate (2×30 ml)
  3. dry with materialthe combined organic extracts were dried (MgSO4)
  4. concentrationThe organic phase was concentrated
  5. dissolutionthe residue was dissolved in 2-propanol (30 ml)
  6. addition4 N HCl (20 ml) was added
  7. temperatureThe mixture was heated
  8. temperatureat reflux temperature for 30 min
  9. stirringstirred at room temperature for 2 hours
  10. concentrationThe reaction mixture was concentrated
  11. dissolutionthe residue was dissolved in ethyl acetate (50 ml)
  12. dry with materialThe organic solution was dried (MgSO4)
  13. customthe solvent was evaporated
  14. customThe oily residue was purified on silica gel (50 g)
  15. washeluting with a mixture of heptane and ethyl acetate (3:2)

Sources & evidence

ORD record
ord-85e3ed54eb7c41949095337b1749c24d
Source dataset
uspto-grants-2007_04
Patent number
US07208497B2

Reaction notes

Loading…