Dimethylformamide → Methyl 2,3-dihydro-8-hydroxy-1,4-benzodioxin-6-carboxylate

HRID 39756Notes

Reaction equation

HRID 39756 reaction equation
CN(C)C=O.[C:6]([O:17][CH3:18])(=[O:16])[C:7]1[CH:15]=[C:13]([OH:14])[C:11]([OH:12])=[C:9]([OH:10])[CH:8]=1.Br[CH2:20][CH2:21]Br.C(=O)([O-])[O-].[K+].[K+]>O>[OH:14][C:13]1[C:11]2[O:12][CH2:20][CH2:21][O:10][C:9]=2[CH:8]=[C:7]([C:6]([O:17][CH3:18])=[O:16])[CH:15]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7428Methyl GallateHCID 78391,2-DibromoethaneHCID 11430Potassium Carbonate

Product 1

HCID 59398158Methyl 2,3-dihydro-8-hydroxy-1,4-benzodioxin-6-carboxylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

To 20 mL of an N,N-dimethylformamide solution containing 2.25 g of methyl gallate, 1.3 mL of 1,2-dibromoethane and 4.05 g of potassium carbonate were added, and the mixture was stirred at 100° C. overnight. The reaction mixture was cooled to room temperature, then fed into water, and the resultant solution was extracted with a mixed solvent of ethyl acetate:toluene of 5:1. The organic layer was washed with water and an aqueous saturated sodium chloride solution, and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to obtain 1.66 g of a brown oily substance, methyl 8-hydroxy-2,3-dihydro-1,4-benzodioxin-6-carboxylate.

Workup

  1. additionwere added
  2. temperatureThe reaction mixture was cooled to room temperature
  3. extractionthe resultant solution was extracted with a mixed solvent of ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialan aqueous saturated sodium chloride solution, and dried over anhydrous magnesium sulfate
  6. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-08a39abd19f9493c9d2dee75623332de
Source dataset
uspto-grants-2013_09
Patent number
US08524738B2

Reaction notes

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