Ethylene Glycol → HCID 11230193, compound

HRID 250502Notes

Reaction equation

HRID 250502 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[OH:10])[CH:5]=[O:6].[CH2:11]([OH:14])[CH2:12][OH:13].C1(C)C=CC(S(O)(=O)=[O:22])=CC=1.[C:26]1([CH3:32])C=CC=CC=1>>[OH:22][CH2:26][CH2:32][O:6][C:5]1([C:4]2[CH:7]=[CH:8][C:9]([OH:10])=[C:2]([CH3:1])[CH:3]=2)[O:14][CH2:11][CH2:12][O:13]1

Participants

5

Reactant 4

HCID 174Ethylene GlycolHCID 1140TolueneHCID 6101p-Toluenesulfonic acidHCID 1399014-Hydroxy-3-methylbenzaldehyde

Product 1

HCID 11230193HCID 11230193, compoundYield 24%

Procedure

A mixture of 3-methyl-p-hydroxybenzaldehyde (0.5 g, 3.6 mmol), ethylene glycol (0.34 g, 5.5 mmol) and p-toluenesulfonic acid (0.07 g, 0.36 mmol) in toluene was heated under reflux. After 24 h, the reaction mixture was cooled to room temperature, TLC showed no starting material. The toluene was removed in vacuo and saturated solution of sodium hydrogen carbonate (20 ml) was added to the residue, which was then extracted with ethyl acetate (3×20 ml). The organic layer was washed with water (20 ml), dried over anhydrous sodium sulfate and the solvent was removed in vacuo. The residue was then recrystallised from an ethyl acetate and hexane mixture to give the product as a brown solid in 24% yield.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux
  3. customThe toluene was removed in vacuo and saturated solution of sodium hydrogen carbonate (20 ml)
  4. additionwas added to the residue, which
  5. extractionwas then extracted with ethyl acetate (3×20 ml)
  6. washThe organic layer was washed with water (20 ml)
  7. dry with materialdried over anhydrous sodium sulfate
  8. customthe solvent was removed in vacuo
  9. customThe residue was then recrystallised from an ethyl acetate and hexane mixture

Sources & evidence

ORD record
ord-05c89c39429243fa98b98b479d573de5
Source dataset
uspto-grants-2011_01
Patent number
US07863313B2

Reaction notes

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