4-Hydroxybenzaldehyde → 4-[2-Hydroxy-2-(2-methoxyphenyl)ethoxy]benzaldehyde

HRID 562949Notes

Reaction equation

HRID 562949 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9]1[CH2:11][O:10]1.[OH:12][C:13]1[CH:20]=[CH:19][C:16]([CH:17]=[O:18])=[CH:15][CH:14]=1.[OH-].[Na+]>C1(C)C=CC=CC=1>[OH:10][CH:9]([C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[O:2][CH3:1])[CH2:11][O:12][C:13]1[CH:20]=[CH:19][C:16]([CH:17]=[O:18])=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 14798Sodium HydroxideHCID 113555722-(2-Methoxyphenyl)oxirane

Product 1

HCID 866450774-[2-Hydroxy-2-(2-methoxyphenyl)ethoxy]benzaldehydeYield 20.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
78 °C

Procedure

To a stirring solution of 2-(2-methoxyphenyl)oxirane (5.60 g, 37.3 mmol) in toluene (65 ml) was added 4-hydroxybenzaldehyde (6.80 g, 56.0 mmol), 1M NaOH (65 ml) and PEG4000 (polyethylene glycol, 0.85 g) and the stirring mixture was heated at 78° C. overnight. The reaction was allowed to cool to RT and it was then extracted with EtOAc (2×150 ml). The combined extracts were washed with brine, dried (Na2SO4), filtered and evaporated in vacuo. The resulting light oil was adsorbed onto silica gel and chromatographed eluting with 30-40% EtOAc/hexanes. There are 2 major spots. Fractions containing the higher Rf spot were combined and evaporated in vacuo to give 1.71 g (17%) the regioisomer as a brown oil. Fractions containing the lower Rf spot were combined and evaporated in vacuo to give 2.05 g (20%) of the title compound as a yellow solid.

Workup

  1. temperatureto cool to RT
  2. extractionit was then extracted with EtOAc (2×150 ml)
  3. washThe combined extracts were washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customchromatographed
  8. washeluting with 30-40% EtOAc/hexanes
  9. additionFractions containing the higher Rf spot
  10. customevaporated in vacuo
  11. customto give 1.71 g (17%) the regioisomer as a brown oil
  12. additionFractions containing the lower Rf spot
  13. customevaporated in vacuo

Sources & evidence

ORD record
ord-4df7604d80c444438700af7f234da3f1
Source dataset
uspto-grants-2011_11
Patent number
US08067450B2

Reaction notes

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