Ethylene Glycol → 2-Phenyl-1,3-dioxolane-2-methanol

HRID 548192Notes

Reaction equation

HRID 548192 reaction equation
[OH:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].[CH2:11](O)[CH2:12][OH:13]>O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C1C=CC=CC=1>[C:5]1([C:3]2([CH2:2][OH:1])[O:13][CH2:12][CH2:11][O:4]2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 2

HCID 174Ethylene GlycolHCID 68490alpha-Hydroxyacetophenone

Product 1

HCID 126142482-Phenyl-1,3-dioxolane-2-methanolYield 98%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 241BenzeneSolvent

Procedure

2-Hydroxy-1-phenylethanone (49.39 g, 297 mmol), ethylene glycol (84 mL, 1500 mmol), p-toluenesulfonic acid monohydrate (1.0 g) and benzene (500 mL) were added to a one-liter eggplant type flask equipped with a Dean-Stark dehydrating device and heated to reflux for 24 hours. The solvent was evaporated in vacuo, water and ethyl acetate were added to the resulting residue and the organic layer was separated. An aqueous layer was further extracted with ethyl acetate twice and the organic layers were combined and washed with a saturated saline solution. It was dried over anhydrous sodium sulfate, the solvent was evaporated therefrom in vacuo and the resulting crude product was purified by a silica gel column chromatography (toluene:ethyl acetate=4:1) to give (2-phenyl-[1,3]dioxolan-2-yl)methanol (52.30 g, 98%) as an oily product. 1H-NMR (DMSO-d6) δ: 3.51 (d, J=6.4 Hz, 2H), 3.74-3.78 (m, 2H), 4.01-4.05 (m, 2H), 4.09 (t, J=6.4 Hz, 1H), 7.28-7.36 (m, 3H), 7.40-7.43 (m, 2H).

Workup

  1. customequipped with a Dean-Stark
  2. temperatureheated
  3. temperatureto reflux for 24 hours
  4. customThe solvent was evaporated in vacuo, water and ethyl acetate
  5. additionwere added to the resulting residue
  6. customthe organic layer was separated
  7. extractionAn aqueous layer was further extracted with ethyl acetate twice
  8. washwashed with a saturated saline solution
  9. dry with materialIt was dried over anhydrous sodium sulfate
  10. customthe solvent was evaporated
  11. customin vacuo and the resulting crude product was purified by a silica gel column chromatography (toluene:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-0605fda638a3412dbce8dd3b39f62728
Source dataset
uspto-grants-2011_05
Patent number
US07939552B2

Reaction notes

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