Water → 2,3-Dihydro-5-methoxy-1,4-benzodioxin

HRID 1440818Notes

Reaction equation

HRID 1440818 reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[CH:8][CH:7]=[C:5]([OH:6])[C:4]=1[OH:10].Br[CH2:12][CH2:13]Br.C(=O)([O-])[O-].[K+].[K+].O>OCC(CO)O.[Cu]>[CH3:1][O:2][C:3]1[C:4]2[O:10][CH2:13][CH2:12][O:6][C:5]=2[CH:7]=[CH:8][CH:9]=1

Participants

7

Reactant 4

HCID 962WaterHCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 136223-Methoxycatechol

Product 1

HCID 743712,3-Dihydro-5-methoxy-1,4-benzodioxin

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 753GlycerolSolvent

Conditions

Temperature
110 °C

Procedure

A heterogeneous mixture containing 1.42 mol of 3-methoxycatechol, 1.57 mol of 1,2-dibromoethane, 1.42 mol of potassium carbonate and 4 g of copper powder in 150 ml of glycerol is heated at 110° C. for 15 hours. After cooling, the mixture is poured into 1 l of water. The aqueous phase is extracted with ethyl ether. The ether phases are then washed with 1N sodium hydroxide, dried and evaporated, and give the expected product.

Workup

  1. temperatureAfter cooling
  2. extractionThe aqueous phase is extracted with ethyl ether
  3. washThe ether phases are then washed with 1N sodium hydroxide
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-3e0e7df9f5d944b48480b7e0c5e1eedc
Source dataset
uspto-grants-1996_03
Patent number
US05500443

Reaction notes

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