4-Hydroxybenzaldehyde → 2-(2-Hydroxyethoxy)-2-(4-hydroxyphenyl)-1,3-dioxolane

HRID 250503Notes

Reaction equation

HRID 250503 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[CH2:10]([OH:13])[CH2:11][OH:12].[C:14]1([CH3:24])C(S([O-])(=O)=O)=CC=CC=1.[NH+]1C=CC=CC=1.O.C1(C)C=CC(S(O)(=O)=[O:39])=CC=1.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1>[OH:39][CH2:14][CH2:24][O:7][C:6]1([C:5]2[CH:8]=[CH:9][C:2]([OH:1])=[CH:3][CH:4]=2)[O:13][CH2:10][CH2:11][O:12]1

Participants

7

Reactant 5

HCID 1264-HydroxybenzaldehydeHCID 174Ethylene GlycolHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 865878692-Methylbenzenesulfonate;pyridin-1-ium

Product 1

HCID 118169822-(2-Hydroxyethoxy)-2-(4-hydroxyphenyl)-1,3-dioxolaneYield 86.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of p-hydroxybenzaldehyde (1 g, 8.18 mmol) in anhydrous toluene (100 mL) was added ethylene glycol (0.68 mL, 12.28 mmol), pyridinium toluene sulphonate (0.2 g, 0.88 mmol) and p-toluene sulphonic acid monohydrate (0.16 g, 0.88 mmol). The solution was refluxed overnight before concentrating the solvent to furnish an amber gum. Saturated sodium bicarbonate (50 mL) was then added to the reaction mixture, and extracted with ethyl acetate (3×50 mL). The organic extracts were dried over magnesium sulphate, filtered, and concentrated to furnish a dark brown gum. The gum was chromatographed on silica (ether/methanol, 9.5:0.5) to furnish the title compound as a dark brown solid (173 mg, 9%).

Workup

  1. temperatureThe solution was refluxed overnight
  2. concentrationbefore concentrating the solvent
  3. customto furnish an amber gum
  4. extractionextracted with ethyl acetate (3×50 mL)
  5. dry with materialThe organic extracts were dried over magnesium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto furnish a dark brown gum
  9. customThe gum was chromatographed on silica (ether/methanol, 9.5:0.5)

Sources & evidence

ORD record
ord-beb7abcf49374129af4fcabb3696625b
Source dataset
uspto-grants-2011_01
Patent number
US07863313B2

Reaction notes

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