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

HRID 1595772Notes

Reaction equation

HRID 1595772 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([C:11]([OH:13])=[O:12])=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1.OS(O)(=O)=O.[C:19](=O)(O)[O-].[Na+]>CO>[CH3:19][O:12][C:11]([C:9]1[CH:8]=[CH:7][C:6]2[O:1][CH2:2][CH2:3][O:4][C:5]=2[CH:10]=1)=[O:13]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 27588331,4-Benzodioxane-6-carboxylic Acid

Product 1

HCID 3802178Methyl 2,3-dihydro-1,4-benzodioxine-6-carboxylateYield 97.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 19.6 g (109 mmol) of 2,3-dihydro-benzo[1,4]dioxine-6-carboxylic acid (J. Chem. Soc., 3445, 1957) in 400 mL of MeOH containing 4 mL of H2SO4 was refluxed overnight. Sodium bicarbonate (18 g) was added, the solvent was removed and the residue was triturated several times with Et2O. The washes were combined, filtered through anhyd MgSO4 and evaporated to yield 20.7 g of the title compound as a pale yellow oil: mass spectrum (electron impact, m/e): 194.

Workup

  1. customthe solvent was removed
  2. customthe residue was triturated several times with Et2O
  3. filtrationfiltered through anhyd MgSO4
  4. customevaporated

Sources & evidence

ORD record
ord-50bece3bff9140228f8ecb8f17cec8aa
Source dataset
uspto-grants-2001_09
Patent number
US06288082B1

Reaction notes

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