Diethyl Ether → 5,8-Dimethyl-1,3-benzodioxane

HRID 1376549Notes

Reaction equation

HRID 1376549 reaction equation
[CH3:1][C:2]1[CH:8]=[CH:7][C:6]([CH3:9])=[C:4](O)[C:3]=1[OH:10].C(=O)([O-])[O-].[K+].[K+].BrC(Br)C.C[CH2:22][O:23][CH2:24]C>C(O)CO>[CH3:9][C:6]1[C:4]2[CH2:24][O:23][CH2:22][O:10][C:3]=2[C:2]([CH3:1])=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 112011,1-DibromoethaneHCID 11430Potassium Carbonate2×HCID 114691143,6-Dimethylbenzene-1,2-diol

Product 1

HCID 218404815,8-Dimethyl-1,3-benzodioxane

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Conditions

Temperature
120 °C

Procedure

To a stirred solution of 3.00 g of 3,6-dimethylcatechol and 6.15 g of potassium carbonate in 35 mL of ethylene glycol is added 3.74 mL of dibromoethane. A reflux condenser is attached and the mixture heated in an oil bath to 120° C. for 4 hours. The mixture is allowed to cool to room temperature and then is distributed between 100 mL of saturated potassium carbonate solution and 200 mL of ether. The ether layer is dried over magnesium sulfate and concentrated under reduced pressure to yield a red liquid, which is purified by chromatography on silica gel to afford 2.90 g of 5,8-dimethyl-1,3-benzodioxane as a light yellow liquid.

Workup

  1. customA reflux condenser is attached
  2. temperatureto cool to room temperature
  3. dry with materialThe ether layer is dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customto yield a red liquid, which
  6. customis purified by chromatography on silica gel

Sources & evidence

ORD record
ord-e11576a9957c42fea5f13cf6a2a300dc
Source dataset
uspto-grants-1997_09
Patent number
US05663189

Reaction notes

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