Ethylene Glycol → 2-Methyl-2-[2-(4-methylbenzene-1-sulfonyl)ethyl]-1,3-dioxolane

HRID 1073837Notes

Reaction equation

HRID 1073837 reaction equation
[C:1]1([CH3:10])[CH:6]=[CH:5][C:4]([S:7]([OH:9])=[O:8])=[CH:3][CH:2]=1.[CH:11]([C:13]([CH3:15])=[O:14])=[CH2:12].N.[CH2:17](O)[CH2:18][OH:19]>>[CH2:18]1[O:19][C:13]([CH2:11][CH2:12][S:7]([C:4]2[CH:5]=[CH:6][C:1]([CH3:10])=[CH:2][CH:3]=2)(=[O:9])=[O:8])([CH3:15])[O:14][CH2:17]1

Participants

5

Reactant 4

HCID 174Ethylene GlycolHCID 222AmmoniaHCID 6570Methyl vinyl ketoneHCID 10818p-Toluenesulfinic acid

Product 1

HCID 125605182-Methyl-2-[2-(4-methylbenzene-1-sulfonyl)ethyl]-1,3-dioxolane

Procedure

A stirred mixture of 4-toluenesulphinic acid (23.7 g, 0.15 mole) and ethylene glycol (30 ml) was treated over 10 minutes with methyl vinyl ketone (6.3 ml, 0.075 mole). The reaction was slightly exothermic and gave a clear solution. This was stirred at room temperature for 6 h, during which time a white precipitate formed. The mixture was poured into ice/water (600 ml) containing conc. ammonia solution (20 ml) and on vigorous stirring a white solid crystallised. This was filtered off, washed with water, dried and recrystallised from propan-2-ol/60-80 petrol to give the title compound (D25) as a white solid (15.2 g, 75%) m.p. 122-123° C. 1H-NMR (CDCl3) δ:

Workup

  1. customgave a clear solution
  2. customformed
  3. stirringon vigorous stirring a white solid
  4. customcrystallised
  5. filtrationThis was filtered off
  6. washwashed with water
  7. customdried
  8. customrecrystallised from propan-2-ol/60-80 petrol

Sources & evidence

ORD record
ord-2d25de96214c493180279d5830ca9341
Source dataset
uspto-grants-1990_11
Patent number
US04971975

Reaction notes

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