3-Methylcatechol → 5-Methyl-1,4-benzodioxane

HRID 1768663Notes

Reaction equation

HRID 1768663 reaction equation
[CH3:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:4]([OH:5])[C:3]=1[OH:9].C(=O)([O-])[O-].[K+].[K+].Br[CH2:17][CH2:18]Br>CN(C)C=O>[CH3:1][C:2]1[C:3]2[O:9][CH2:18][CH2:17][O:5][C:4]=2[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 3403-MethylcatecholHCID 78391,2-DibromoethaneHCID 11430Potassium Carbonate

Product 1

HCID 122388275-Methyl-1,4-benzodioxaneYield 82%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
125 °C

Procedure

In 300 ml of dry dimethylformamide, was dissolved 30 g of 3-methylcatechol and then 100 g of potassium carbonate was added to the solution. This solution was heated to 120 to 130° C. and 136 g of 1,2-dibromoethane was added dropwise in ten and several portions. After stirring for 30 minutes under the same conditions, the mixture was cooled and solid materials were removed by filtration. To the filtrate, was added diethyl ether, and the mixture was washed successively with a 3% sodium hydroxide aqueous solution, water and saturated saline solution, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The resulting oily material was purified by silica gel column chromatography to obtain 29.7 g of the titled 5-methyl-1,4-benzodioxane (yield: 82%) .

Workup

  1. temperaturethe mixture was cooled
  2. customsolid materials were removed by filtration
  3. additionTo the filtrate, was added diethyl ether
  4. washthe mixture was washed successively with a 3% sodium hydroxide aqueous solution, water and saturated saline solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was removed under reduced pressure
  7. customThe resulting oily material was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-4abece4a877346159d794cdd8f62f7da
Source dataset
uspto-grants-1995_01
Patent number
US05378726

Reaction notes

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