1,2-Dibromoethane → 8-Methoxy-2,3-dihydrobenzo[b][1,4]dioxine-5-carboxylic Acid

HRID 2285484Notes

Reaction equation

HRID 2285484 reaction equation
[OH:1][C:2]1[C:10]([OH:11])=[C:9]([O:12][CH3:13])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH2:14](Br)[CH2:15]Br>O>[CH3:13][O:12][C:9]1[C:10]2[O:11][CH2:14][CH2:15][O:1][C:2]=2[C:3]([C:4]([OH:6])=[O:5])=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 78391,2-DibromoethaneHCID 775342,3-Dihydroxy-4-methoxybenzoic acid

Product 1

HCID 227342488-Methoxy-2,3-dihydrobenzo[b][1,4]dioxine-5-carboxylic AcidYield 57%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

171.5 g of 2,3-dihydroxy-4-methoxy benzoic acid, 515 cm3 of alcohol, 280 cm3 of soda lye and 175 g of ethylene bromide were introduced into a balloon flask provided with an agitator, a thermometer and an inlet pipe for nitrogen. The mixture was heated under reflux and then cooled and poured into 2.8 liters of water. The solution was filtered and treated with 85 cm3 of concentrated hydrochloric acid. The pecipitate was dried off, washed and dried. After recrystallization in dimethylformamide, 110 g, of 8-methoxy-1,4-benzodioxane-5-carboxylic acid were obtained (M.P.: 224°-226° C.; yield: 57%).

Workup

  1. customprovided with an agitator
  2. temperatureThe mixture was heated
  3. temperatureunder reflux
  4. temperaturecooled
  5. filtrationThe solution was filtered
  6. additiontreated with 85 cm3 of concentrated hydrochloric acid
  7. customThe pecipitate was dried off
  8. washwashed
  9. customdried
  10. customAfter recrystallization in dimethylformamide

Sources & evidence

ORD record
ord-da5139dd4cb54205aea1feb8d3edee34
Source dataset
uspto-grants-1982_04
Patent number
US04323503

Reaction notes

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