3-Hydroxybenzaldehyde → Benzaldehyde, 3-(2-hydroxyethoxy)-

HRID 1694582Notes

Reaction equation

HRID 1694582 reaction equation
CS(C)=O.[OH:5][C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][CH:13]=1)[CH:9]=[O:10].C1(=O)O[CH2:17][CH2:16][O:15]1.C(=O)([O-])[O-].[K+].[K+]>C(OC(C)C)(=O)C.O>[OH:15][CH2:16][CH2:17][O:5][C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][CH:13]=1)[CH:9]=[O:10]

Participants

7

Reactant 4

HCID 1013-Hydroxybenzaldehyde2×HCID 679Dimethyl SulfoxideHCID 7303Ethylene carbonateHCID 11430Potassium Carbonate2×

Product 1

HCID 6453965Benzaldehyde, 3-(2-hydroxyethoxy)-

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7915Isopropyl AcetateSolvent

Procedure

To a 5 L flask equipped with an internal temperature probe and a mechanical stirrer was added dimethyl sulfoxide (500 mL), 3-hydroxybenzaldehyde (100.0 g, 0.819 mol), ethylene carbonate (108 g, 1.23 mol), and potassium carbonate (136 g, 0.983 mol). The resulting mixture was stirred at 110 to 125° C. until all 3-hydroxybenzaldehyde starting material was consumed. (Additional portions of ethylene carbonate may be added to drive the reaction to completion). The reaction mixture was then cooled to below 25° C. and diluted with isopropyl acetate (1.0 L) and water (1.5 L). The mixture was stirred until the residual potassium carbonate was completely dissolved. The layers were separated and the organic layer was washed with an additional portion of water (1.5 L). Additional isopropyl acetate was added (1.0 L), and then distilled off to leave a final volume of ˜1 L of dry organic solution of 3-(2-hydroxyethoxy)benzaldehyde.

Workup

  1. customTo a 5 L flask equipped with an internal temperature probe and a mechanical stirrer
  2. customwas consumed
  3. addition(Additional portions of ethylene carbonate may be added
  4. customthe reaction to completion)
  5. temperatureThe reaction mixture was then cooled to below 25° C.
  6. dissolutionwas completely dissolved
  7. customThe layers were separated
  8. washthe organic layer was washed with an additional portion of water (1.5 L)
  9. additionAdditional isopropyl acetate was added (1.0 L)
  10. distillationdistilled off

Sources & evidence

ORD record
ord-b28ff023406e419abc81a762dcaa3962
Source dataset
uspto-grants-2012_04
Patent number
US08158796B2

Reaction notes

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