1,2-Dibromoethane → Methyl 2,3-dihydro-1,4-benzodioxine-6-carboxylate

HRID 596602

Reaction equation

HRID 596602 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([OH:11])[CH:5]=1.C[O-].[Na+].Br[CH2:17][CH2:18]Br>CO>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]2[O:10][CH2:17][CH2:18][O:11][C:6]=2[CH:5]=1

Participants

5

Reactant 3

HCID 78391,2-DibromoethaneHCID 287064Methyl 3,4-DihydroxybenzoateHCID 10942334Sodium Methoxide

Product 1

HCID 3802178Methyl 2,3-dihydro-1,4-benzodioxine-6-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 4.20 g. of 3,4-dihydroxybenzoic acid methyl ester in 10.0 ml. of methanol is combined with 7.0 g. of sodium methoxide and then 15.0 g. of 1,2-dibromoethane is added. The resulting mixture is refluxed under nitrogen for 24 hours, then cooled, filtered, evaporated in vacuo and the resulting oil dissolved in 50 ml. of chloroform. The resulting solution after again filtering is chromatographed over 100 ml. of silica gel eluting with chloroform to obtain 3,4-ethylenedioxybenzoic acid methyl ester, m.p. 43°-45° C.

Workup

  1. temperatureThe resulting mixture is refluxed under nitrogen for 24 hours
  2. temperaturecooled
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. dissolutionthe resulting oil dissolved in 50 ml
  6. filtrationThe resulting solution after again filtering
  7. customis chromatographed over 100 ml

Sources & evidence

ORD record
ord-a68d6c679ea04501b26a9aae8c2ed78d
Source dataset
uspto-grants-1977_03
Patent number
US04011323

Linked notes

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