2-Methylbenzenesulfonic acid → 2-Bromomethyl-4,5-dimethyl-1,3-dioxolane

HRID 127131Notes

Reaction equation

HRID 127131 reaction equation
[Br:1][CH2:2][CH:3]([O:6]C)[O:4]C.C1(C)C(S(O)(=O)=O)=[CH:10][CH:11]=[CH:12][CH:13]=1.C(=O)([O-])[O-].[K+].[K+]>>[Br:1][CH2:2][CH:3]1[O:6][CH:12]([CH3:13])[CH:11]([CH3:10])[O:4]1

Participants

4

Reactant 3

HCID 69252-Methylbenzenesulfonic acidHCID 11430Potassium CarbonateHCID 816722-Bromo-1,1-dimethoxyethane

Product 1

HCID 128944572-Bromomethyl-4,5-dimethyl-1,3-dioxolane

Procedure

2-Bromo-1,1-dimethoxyethane (188 grams) 2,3-butanediol (100 grams) and toluene sulfonic acid (0.1 grams) were charged into a glass reaction vessel fitted with a mechanical stirrer, thermometer, and reflux condenser. The reaction mixture was heated to reflux for a period of about 2 hours. It was then cooled to room temperature, neutralized with potassium carbonate, and filtered. The filtrate was distilled, the desired product 2-bromomethyl-4,5-dimethyl-1,3-dioxolane being obtained as a fraction boiling at 82° C.-85° C. at a pressure of about 12 mm Hg.

Workup

  1. customfitted with a mechanical stirrer
  2. temperaturethermometer, and reflux condenser
  3. temperatureThe reaction mixture was heated
  4. temperatureto reflux for a period of about 2 hours
  5. filtrationfiltered
  6. distillationThe filtrate was distilled

Sources & evidence

ORD record
ord-2902b9cb8c9b4509b6cf6aa24edbe88f
Source dataset
uspto-grants-1981_03
Patent number
US04255182

Reaction notes

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