Ethylene Glycol → [4-(1,3-Dioxolan-2-yl)phenyl]methanol

HRID 332670Notes

Reaction equation

HRID 332670 reaction equation
[CH:1]1[C:6]([CH:7]=[O:8])=[CH:5][CH:4]=[C:3]([CH:9]=[O:10])[CH:2]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:23](O)[CH2:24][OH:25].[BH4-].[Na+]>C1(C)C=CC=CC=1.C(O)C>[O:8]1[CH2:23][CH2:24][O:25][CH:7]1[C:6]1[CH:5]=[CH:4][C:3]([CH2:9][OH:10])=[CH:2][CH:1]=1

Participants

7

Reactant 4

HCID 174Ethylene GlycolHCID 12173TerephthalaldehydeHCID 521998p-Toluenesulfonic acid monohydrateHCID 4311764Sodium borohydride

Product 1

HCID 15192333[4-(1,3-Dioxolan-2-yl)phenyl]methanolYield 48%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of terephthaldehyde (5.4 g, 40 mmol), para-toluenesulfonic acid—monohydrate (0.4 g, 2 mmol), and ethylene glycol in toluene (80 mL) was heated at 110° C. for 4 hours. The reaction mixture was allowed to cool and was washed with saturated sodium hydrogen carbonate and dried with anhydrous magnesium sulphate. The filtrate was evaporated at reduced pressure to afford a oil. The oil was dissolved in ethanol (200 mL), and then the reaction mixture cooled to 0° C. Sodium borohydride (5.9 g, 160 mmol) was added portionwise, and the resultant reaction mixture allowed to warm to ambient temperature over 16 hours. The reaction mixture was quenched with saturated sodium hydrogen carbonate and subsequently extracted twice with ethyl acetate. The combined organic extracts were dried with anhydrous magnesium sulphate, and the solvent evaporated at reduced pressure. The crude material was purified by silica gel chromatography eluting with 100% iso-hexane to 50% ethyl acetate in iso-hexane to afford the title compound as a colourless oil (3.4 g, 48%).

Workup

  1. temperatureto cool
  2. washwas washed with saturated sodium hydrogen carbonate
  3. dry with materialdried with anhydrous magnesium sulphate
  4. customThe filtrate was evaporated at reduced pressure
  5. customto afford a oil
  6. temperaturethe reaction mixture cooled to 0° C
  7. customthe resultant reaction mixture
  8. temperatureto warm to ambient temperature over 16 hours
  9. customThe reaction mixture was quenched with saturated sodium hydrogen carbonate
  10. extractionsubsequently extracted twice with ethyl acetate
  11. dry with materialThe combined organic extracts were dried with anhydrous magnesium sulphate
  12. customthe solvent evaporated at reduced pressure
  13. customThe crude material was purified by silica gel chromatography
  14. washeluting with 100% iso-hexane to 50% ethyl acetate in iso-hexane

Sources & evidence

ORD record
ord-0d6bcae2c821408f9410a27e22d823da
Source dataset
uspto-grants-2014_11
Patent number
US08877774B2

Reaction notes

Loading…