Potassium Carbonate → 5-(2,2-Diethoxyethoxy)-2,3-dihydro-1,4-benzodioxin

HRID 2392608Notes

Reaction equation

HRID 2392608 reaction equation
[OH:1][C:2]1[C:11]2[O:10][CH2:9][CH2:8][O:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.Br[CH2:13][CH:14]([O:18][CH2:19][CH3:20])[O:15][CH2:16][CH3:17].C(=O)([O-])[O-].[K+].[K+]>CN(C)C(=O)C>[CH2:16]([O:15][CH:14]([O:18][CH2:19][CH3:20])[CH2:13][O:1][C:2]1[C:11]2[O:10][CH2:9][CH2:8][O:7][C:6]=2[CH:5]=[CH:4][CH:3]=1)[CH3:17]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 74852Ethane, 2-bromo-1,1-diethoxy-HCID 825202,3-Dihydro-1,4-benzodioxin-5-ol

Product 1

HCID 189802705-(2,2-Diethoxyethoxy)-2,3-dihydro-1,4-benzodioxinYield 60.2%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 2,3-dihydro-5-hydroxy-1,4-benzodioxin (0.13 mol), 2-bromo- 1,1-diethoxyethane (0.13 mol) and potassium carbonate (0.13 mol) in N,N-dimethyl- acetamide (250 ml) was stirred overnight at 140° C. The solvent was evaporated. The residue was partitioned between 1,1'-oxybisethane and water. The organic layer was separated, washed with a saturated NaCl solution, dried (MgSO4), filtered and the solvent was evaporated. The residual oil was crystallized from 2,2'-oxybispropane. The precipitate was filtered off and dried, yielding 21 g (60.2%) 5-(2,2diethoxyethoxy)-2,3- dihydro-1,4-benzodioxin; mp. 73.1° C. (interm.11).

Workup

  1. customThe solvent was evaporated
  2. customThe residue was partitioned between 1,1'-oxybisethane and water
  3. customThe organic layer was separated
  4. washwashed with a saturated NaCl solution
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customthe solvent was evaporated
  8. customThe residual oil was crystallized from 2,2'-oxybispropane
  9. filtrationThe precipitate was filtered off
  10. customdried

Sources & evidence

ORD record
ord-837c164f678f48698913fc95116c9147
Source dataset
uspto-grants-1998_09
Patent number
US05801179

Reaction notes

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