Water → Methyl 3,4-dihydro-2H-benzo-1,5-dioxepin-6-carboxylate

HRID 1610240Notes

Reaction equation

HRID 1610240 reaction equation
[OH:1][C:2]1[C:11]([OH:12])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].Br[CH2:14][CH2:15][CH2:16]Br.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[O:12]1[C:11]2[CH:10]=[CH:9][CH:8]=[C:3]([C:4]([O:6][CH3:7])=[O:5])[C:2]=2[O:1][CH2:16][CH2:15][CH2:14]1

Participants

6

Reactant 4

HCID 962WaterHCID 80011,3-DibromopropaneHCID 11430Potassium CarbonateHCID 75484Methyl 2,3-Dihydroxybenzoate

Product 1

HCID 6455320Methyl 3,4-dihydro-2H-benzo-1,5-dioxepin-6-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl 2,3-dihydroxybenzoate (1.870 g, 11.12 mmol), 1,3-dibromopropane (2.25 g, 11.1 mmol) and potassium carbonate (6.15 g, 44.5 mmol) were stirred in N,N-dimethylformamide (20 ml) overnight at 60° C. The reaction solution was poured into water and extracted twice with ethyl acetate. The collected organic layer was dried over anhydrous sodium sulfate and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=6/1−3/1) to give the objective substance.

Workup

  1. extractionextracted twice with ethyl acetate
  2. dry with materialThe collected organic layer was dried over anhydrous sodium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=6/1−3/1)
  5. customto give the objective substance

Sources & evidence

ORD record
ord-c14725635d004efa904fcc455855642f
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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