2-Methylbenzenesulfonic acid → 2-Bromomethyl-4-methyl-1,3-dioxane

HRID 127133

Reaction equation

HRID 127133 reaction equation
[Br:1][CH2:2][CH:3](OC)OC.[CH2:8]([OH:13])[CH2:9][CH:10]([OH:12])[CH3:11].C1(C)C(S(O)(=O)=O)=CC=CC=1>>[Br:1][CH2:2][CH:3]1[O:12][CH:10]([CH3:11])[CH2:9][CH2:8][O:13]1

Participants

4

Reactant 3

HCID 69252-Methylbenzenesulfonic acidHCID 78961,3-ButanediolHCID 816722-Bromo-1,1-dimethoxyethane

Product 1

HCID 99902352-Bromomethyl-4-methyl-1,3-dioxane

Procedure

2-Bromo-1,1-dimethoxyethane (0.1 mole) and 1,3-butanediol (0.1 mole) are charged into a glass reaction vessel fitted with a mechanical stirrer, thermometer, Dean Stark trap and reflux condenser. Toluene sulfonic acid (0.1 grams) is added and the reaction mixture is heated and alcohol removed. When alcohol evolution ceases, the reaction mixture is then cooled to room temperature, treated with sodium carbonate (5 grams) and filtered. Volatiles are stripped from the filtrate using a rotary evaporator to yield the desired product 2-bromomethyl-4-methyl-1,3-dioxane as the residue.

Workup

  1. customfitted with a mechanical stirrer
  2. temperaturethermometer, Dean Stark trap and reflux condenser
  3. temperaturethe reaction mixture is heated
  4. customalcohol removed
  5. additiontreated with sodium carbonate (5 grams)
  6. filtrationfiltered
  7. customa rotary evaporator

Sources & evidence

ORD record
ord-1ad4f162cba04b13afc719abe876680b
Source dataset
uspto-grants-1981_03
Patent number
US04255182

Linked notes

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