Catechol → 3-Methylene-3,4-dihydro-2H-1,5-benzodioxepin

HRID 1597435Notes

Reaction equation

HRID 1597435 reaction equation
[C:1]1([C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4])[OH:2].C([O-])([O-])=O.[Cs+].[Cs+].Cl[CH2:16][C:17]([CH2:19]Cl)=[CH2:18]>CN(C=O)C>[CH2:16]=[C:17]1[CH2:19][O:4][C:3]2[CH:5]=[CH:6][CH:7]=[CH:8][C:1]=2[O:2][CH2:18]1

Participants

5

Reactant 3

HCID 289CatecholHCID 10796Cesium carbonateHCID 158593-Chloro-2-chloromethyl-1-propene

Product 1

HCID 5954503-Methylene-3,4-dihydro-2H-1,5-benzodioxepin

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of catechol (4.4 g, 40 mmol), Cs2CO3 (27.7 g, 85 mmol) and 3-chloro-2 chloromethyl-prop-1-ene(5 g, 40 mmol) in DMF (80 mL) was striired overnight at rt. The reaction was partitioned between ether and water and the organic extract was washed with brine, dried (MgSO4), filtered and concentrated to 5.46 g (84%) of a yellow oil. MS 163 (M+H)+.

Workup

  1. customThe reaction was partitioned between ether and water
  2. extractionthe organic extract
  3. washwas washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated to 5.46 g (84%) of a yellow oil

Sources & evidence

ORD record
ord-b53199d70300423d93f0b1b1129052be
Source dataset
uspto-grants-2001_09
Patent number
US06294573B1

Reaction notes

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